Process Research and Development, Bristol Myers Squibb Pharmaceutical Research Institute One Squibb Drive, New Brunswick, New Jersey 08903
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1 A Mechanistic Study on the Amidation of Esters Mediated by Sodium Formamide Antonio Ramirez,* Boguslaw Mudryk, Lucius Rossano, Srinivas Tummala Process Research and Development, Bristol Myers Squibb Pharmaceutical Research Institute ne Squibb Drive, ew Brunswick, ew Jersey Supporting Information Table of Contents Page I. Representative Reaction Profile for the Amidation of Ester 4 S2 II. Amidation of Ester 4 as Monitored by 13 C MR III. Spectroscopic Data for the Characterization of Compounds 4 and 5 IV. IR Titration Experiments S3 S4 S9 V. Kinetic Studies S10 VI. B3LYP and MP2 Calculations A. Computational methods B. Calculated MP2 energies C. Calculated coordinates VII. References S14 S25 S1
2 I. Representative Reaction Profile for the Amidation of Ester % Conversion Time (min) Percent conversion versus time for the amidation of ester 4 (0.023 M) with 0.27 M Mea and 0.57 M formamide in DMF at 22.5 C as monitored by PLC ( symbols represent ester 4, symbols represent carboxamide 6, symbols represent acylformamide 5). S2
3 II. Amidation of Ester 4 as Monitored by 13 C MR a Representative amidation of ester 4 (0.40 M) with 0.40 M Mea and 3.60 M formamide in DMF d7 at 25.0 C as monitored by 13 C MR to confirm the formation of sodium diformylamide. (a) Before the addition of Mea; (b) 10 min after the addition of Mea; (c) 30 min after the addition of Mea; (d) 13 C MR spectrum of commercially available sodium diformylamide (0.1 M) in formamide and DMF d7. S3
4 III. Spectroscopic Data for the Characterization of Compounds 4 and 5. S4
5 4 C 2 Me Me S5
6 S6
7 S7
8 C 2 Me 4 Me Protonated form of 5 Me S8
9 IV. IR Titration Experiments A B A. verlay of IR spectra showing diagnostic bands 1 for C2 (1710 cm 1, solid line) and Ca (1580 cm 1, dashed line) in DMF. The disappearance of C2 and concomitant formation of Ca were readily monitored using a ReactIR system fitted with a SiComp probe. B. Representative titration of a solution of C2 in DMF (2.27 M) with a solution of Mea in Me (4.4 M) at C. The deprotonation occurred instantaneously upon addition of Mea at 0 C to afford Keq = The reported error values for Keq correspond to an average deviation of three measurements. S9
10 V. Kinetic Studies 4 6 Representative overlay of PLC traces with UV detection at 280 nm for the amidation of methyl ester 4 at 1 min intervals. [4] = M; [Ca] = M; [Me] = M; [C2] = 4.0 M. Analogous plots normalized to o xylene internal standard were used to calculate the initial rates within the first 0 15% of substrate conversion using a linear fit. S10
11 Initial rates versus [4] for the amidation of 4 with Ca (0.027 M) and DMF cosolvent at 0 C ([Me] = 0.46 M; [C2] = 4.8 M). The curve depicts an unweighted least squares fit to Δ[4]/Δt = k[4] n (k = ; n = ). [4] (M) Δ[4]/Δt (M. s 1 ) ± 3E ± 7E ± 5E ± 1E ± 2E 3 Δ[4]/Δt x 10 2 (M/s) [4] (M) Initial rates versus [Ca] for the amidation of 4 at 0 C ([4] = M; [Me] = 0.46 M; [C2] = 4.8 M). The curve depicts an unweighted leastsquares fit to Δ[4]/Δt = k[4] n (k = ; n = ). [Ca] (M) Δ[4]/Δt (M. s 1 ) ± 1E ± 1E ± 8E ± 9E ± 5E 4 Δ[4]/Δt x 10 2 (M/s) [Ca] (M) S11
12 Initial rates versus [Me] for the amidation of 4 at 0 C ([4] = M; [Ca] = M; [C2] = 4.8 M). The curve depicts an unweighted least squares fit to Δ[4]/Δt = a[me]/k + [Me) (a = Ms 1 ; k = ). [Me] (M) Δ[4]/Δt (Ms 1 ) ± 1E ± 1E ± 2E ± 1E ± 4E ± 3E ± 3E 4 Δ[4]/Δt x 10 3 (M/s) [Me] (M) Initial rates versus [C2] for the amidation of 4 at 0 C ([4] = M; [Ca] = M; [Me] = 0.46 M). The curve depicts an unweighted least squares fit to Δ[4]/Δt = a[c2]/k + [C2] (a = Ms 1 ; k = ). [C2] (M) Δ[4]/Δt (Ms 1 ) ± 1E ± 2E ± 3E ± 2E ± 2E ± 3E ± 2E 4 Δ[4]/Δt x 10 3 (M/s) [C 2 ] (M) S12
13 Arrhenius plot for the amidation of 4 with Ca (0.027 M) and DMF cosolvent over a 40 C temperature range ([4] = M; [Me] = 0.46 M; [C2] = 4.8 M). The curve depicts an unweighted least squares fit to ln k = Ea/R (1/T) + ln A (Ea = , ln A = ). Plot correlation coefficient R = /T (K 1 ) ln k (Ms 1 ) ln k (M/s) /T x 10 2 (K -1 ) ammett plot for the amidation of a series of p substituted methyl benzoates with Ca (0.027 M) and DMF cosolvent at 0 C temperature range ([ester] = M; [Me] = 0.46 M; [C2] = 4.8 M). The curve depicts an unweighted least squares fit to log (kx/k) = σρ + A (ρ = ; A = ). 2 Plot correlation coefficient R = σ (X) log (kx/k) 0 () (Me2) (Me) (Me) (F) (Cl) (Br) (2) 2.68 log (k X /k ) Br 1 -F -Me -Cl 0 -Me -Me σ S13
14 VI. B3LYP and MP2 Calculations A. Computational Methods. All calculations were executed using Gaussian 09, Revision B A series of geometries were systematically tested for reactants, intermediates, products and transition structures at the B3LYP/6 31+G(d) level, and the lowest energy forms were submitted to single point MP2/6 31+G(d) calculations incorporating Tomasi s Polarized Continuum Model (PCM) corrections 4 for formamide 5 as the bulk solvent. The calculation of solution phase energies using gas phase geometries has been reported previously. 6 All transition structures were reoptimized after the explicit addition of a molecule of formamide as coordinating solvent, and the resulting structures were only considered when their energies were lower than those of the unsolvated analogues. The calculated energies (ΔG, K, 1.0 atm) result from the sum of single point MP2/6 31+G(d)//B3LYP/6 31+G(d) calculations, thermal corrections to Gibbs free energy (TCGFE) as obtained from the frequency analysis at the B3LYP/6 31+G(d) level, and PCM corrections. The overall reaction profile incorporating PCM calculations is presented in Figure 3. Energy values are given relative to the separated ester 7 and sodium formamide reactants in kcal. mol 1. In the absence of structural data on the aggregation and solvation states of sodium formamide and plausible intermediates under the reaction conditions, these energies represent reactivity trends rather than precise values. Frequency calculations for all stationary points were carried out to describe them either as minima (i = 0) or as first order transition states (i = 1). For all transition structures, visualization of the imaginary frequencies corresponded to the expected normal mode for the elementary step under investigation. Intrinsic reaction coordinate calculations (IRC) were performed from the transition states in forward and reverse directions to confirm the lowest energy reaction pathways that connect the corresponding minima. S14
15 B. Calculated MP2 Energies Structure a TCGFE (artree) MP2/PCM (artree) ΔG (kcal. mol 1 ) Imaginary ν (cm 1 ) Me Mea C Ca TS TS TS3a TS3b TS3c TS3d TS TS5a TS5b TS5c TS (C)2a a Multiple unconstrained searches for an stationary point corresponding to TS3a failed to converge. An alternative relaxed-scan approximation 7 by lengthening the C()- bond affords a flat potential energy surface associated with structures that display dissociation energies ~ 30 kcal. mol -1. S15
16 C. Calculated Coordinates Me Mea C C2 C a Ca C C a C C C C C C C C C C C S16
17 C C a C C C C a C C C S17
18 Me Me a C C C C a C C C C C C C C C C C a S18
19 C C C C C a C C C C C C a C a C S19
20 C C C C C a C a C C C C a C a C C C C S20
21 Me a a TS6 C C C a C a C C C C C C C C a C a C S21
22 a(c)2 Me 12 a C C C C a C C C a Me Me a TS3c C C C C a C C C S C C C C a C C C
23 Me Me a Me TS3d Me Me TS3e a C C C C a C C C C C C C C a C C C C S23
24 Me a TS5b a Me TS5c a a C C C C C a C a C C C C C a C a C C C S24
25 VII. References (1) (a) Correa,. M.; Pires, P. A. R.; Silber, J. J.; El Seoud,. A. J. Phys. Chem. B 2005, 109, (b) ast, R.; Dilly, P. Angew. Chem. Int. Ed. 1967, 6, 357. (c) Evans, J. C. J. Chem. Phys. 1954, 22, (2) σ values taken from: Ritche, C. D.; Sager, W. F. Prog. Phys. rg. Chem. 1964, 2, (3) Frisch, M. J.; Trucks, G. W.; Schlegel,. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; akatsuji,.; Caricato, M.; Li, X.; ratchian,. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; ada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; asegawa, J.; Ishida, M.; akajima, T.; onda, Y.; Kitao,.; akai,.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; gliaro, F.; Bearpark, M.; eyd, J. J.; Brothers, E.; Kudin, K..; Staroverov, V..; Keith, T.; Kobayashi, R.; ormand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega,.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev,.; Austin, A. J.; Cammi, R.; Pomelli, C.; chterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas,.; Foresman, J. B.; rtiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford CT, (4) (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, (b) Tomasi, J.; Bonaccorsi, R.; Cami, R.; de Valle, F. J.. J. Mol. Struct. 1991, 234, (5) Internal parameters provided by Gaussian 09 were used to model the formamide solvent medium (ε = ). (6) (a) Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, (b) Dudnik, A. S.; Xia, Y.; Li, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, (c) Wheeler, S. E.; Mceil, A. J.; Müller, P.; Swager, T. M.; ouk, K.. J. Am. Chem. Soc. 2010, 132, (7) For related examples, see: (a) Fressigné, C.; Lautrette, A.; Maddaluno, J. J. rg. Chem. 2005, 70, (b) Pomelli, C. S.; Bianucci, A. M.; Crotti, P.; Favero, L. J. rg. Chem. 2004, 69, (c) Gillies, M. B.; Tønder, J. E.; Tanner, D.; orrby, P. J. rg. Chem. 2002, 67, S25
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