Lecture'15:'March'21,'2013
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1 CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie S C 3 C 3 cimetidine (Tagement) C Lecture'15:'March'21,'2013 Synthesis*of*Amines*(24.1) eac8ons*of*amines**( )
2 Basicity)in)Drug)Development bservation: istamine binds to 2 receptor causing release of gastric acids (agonist) esearch goals: Find target that binds to 2 receptor stopping production of gastric acids (antogonist) 2 2 histamine -Guanylhistamine first compound to show any antagonist activity rganic Chemistry II (CM 224) Slide 7
3 Drug)Development 2 2 C 3 -Guanylhistamine burimamide S first compound to show any antagonist activity but, protonated at physiological p neutral at phys. p and effective antagonist in rats pk a = pk a = 7.3 C 3 histamine burimamide S Burimamide was first agonist tested in humans, but showed no activity. Medicinal chemists noted that burimamide was a stronger base than histamine. They set out to modify its structure in order to reduce it s basicity to more closely resemble histamine. rganic Chemistry II (CM 224) Slide 8
4 Your)Turn pk a = 7.3 burimamide S C 3 In your team: elect a senior scientist (board writer and defender) and then propose a drug with structural changes that would reduce the basicity of burimamide (increase the acidity of its conjugate acid). You may change anything about the side chain and only groups attached to the imadazole ring. C 3 S S C 3 Showed 9x activity of burimamide, but lowered WBC counts. It was thought to be caused by thiourea group. metiamide S: EWG increases PE of conjugate acid (stronger) C3: increases electron density on (more basic) isoteric replacement: replacement of a group with roughly same volume, but different electronic properties rganic Chemistry II (CM 224) Slide 9
5 Your)Turn pk a = 7.3 burimamide S C 3 In your team: elect a senior scientist (board writer and defender) and then propose two drugs with structural changes that would reduce the basicity of burimamide (increase the acidity of its conjugate acid). You may change anything about the side chain and groups attached to the imadazole ring. S C 3 S C 3 C 3 metiamide S C 3 cimetidine (Tagement) C S: EWG increases PE of conjugate acid (stronger) C3: increases electron density on (more basic) Cyanoguanidine: cyano group delocalizes lone-pair, reducing it basicity so its not protonated at phys. p sold in US 1979 Glaxo-Smith-Kline first blockbuster drug ($1 billion/yr) rganic Chemistry II (CM 224) Slide 10
6 CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie 2 3 C C 3 3 C C 3 2º alcohol 1º amine Synthesis'of' Primary'Amines 24.6
7 Synthesis)of)Primary)Amines 1. LA eduction of itriles C a. LiAl 4, TF b. 3 + / LA eduction of Azides a. LiAl 4, TF b. 3 + / LA eduction of Amides 1. SCl 2, Et 2 2 a. LiAl 4, TF 2 b. 3 b. 3 + / 2 rganic Chemistry II (CM 224) Slide 12
8 2 C Synthesis)of)Amines)by)educ-on chain extension! Br 2 no chain extension 2 2 no chain extension rganic Chemistry II (CM 224) Slide 13
9 Why)ot)Alkyla-on? 2 Br vs. 2 3 or X 2 alkylation of ammonia or amide Br rganic Chemistry II (CM 224) Slide 14
10 Alkyla-on)of)Amines In theory... S X 3 X a 2 S X 2 X a + X S 2 X a S 2 + X X rganic Chemistry II (CM 224) Slide 15
11 veralkyla-on)is)common + Br octylamine (45%) dioctylamine (43%) 3 initially formed primary amine has approximately same nucleophilicity as ammonia (3) and undergoes 2nd alkylation to give dioctylamine even 2º and 3º amines can undergo alkylation to give quaternary ammonium salts rganic Chemistry II (CM 224) Slide 16
12 Synthesis)of)Primary)Amines:)Another)Alterna-ve 4. Gabriel Amine Synthesis with Phthalimide K eq = K K + + phthalimide (pka = 8.3) -potassiophthalimide water (pka = 15.7) Cl phthalhydrazide + 2 benzylamine (1º amine) a/2 (hydrolysis) or 2 2 (hydrazine) -benzylphthalimide rganic Chemistry II (CM 224) Slide 17
13 Alkyl)Phthalimide)ydrolysis)Mechanism Board Work: 1. ydrazine (more common) a much better nucleophile than hydroxide. 2. ydrazine very weak base (pka of CA = 8). 3. ucleophilic Acyl Substitution (addition-elimination). rganic Chemistry II (CM 224) Slide 18
14 Synthesis)of)Primary)Amines 5. Curtius earrangement of Acyl Azides C Cl a 3 C C + acid chloride acyl azide 1º amine carbon dioxide nitrogen 1. SCl 2 2. a Cl 1. SCl 2 2. a works for aryl and alkyl acyl azides acyl azide is not typically isolated overall, loss of one carbon atom in the transformation (C2) rganic Chemistry II (CM 224) Slide 20
15 Cur-us)Mechanism Board Work: 1. Lewis structure of azide. 2. ucleophilic acyl substitution. 3. Carbon migration & loss of Isocyanate intermediate. 5. Decarboxylation. rganic Chemistry II (CM 224) Slide 21
16 Chiral)Amines 3 C 3 C 1. SCl 2 2. a SCl 2 2. a C 3 C C retention of configuration is observed at the a-carbon of the carboxylic acid chiral amines can be prepared rganic Chemistry II (CM 224) Slide 22
17 CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie eacions'of'amines 24.7
18 eview:)eac-ons)of)amines 2 C3I 3 C C 3 I C C Cl C 3 alkylation acylation 3 substitution 2 3 C Cl reductive amination rganic Chemistry II (CM 224) Slide 25
19 eview:)educ-ve)amina-on C 3 2 C 3 2, i (M) C3 or ab 4 or acb 3 2, i (M) or ab 4 or acb 3 works for ammonia (3), primary amines (-2) and secondary amines (2-) proceeds through imine or imminium ion (no enamine) intermediate reduction by hydrogenation (2, metal) or borohydride (B4 ) rganic Chemistry II (CM 224) Slide 26
20 eview:)educ-ve)amina-on C C C 3 3 L-glutamate L-glutamate-5-semialdehyde spontaneous condensation 2 L-proline C reduction (add ": ") ADP " " + C 2 2 rganic Chemistry II (CM 224) Slide 27
21 offmann)elimina-on I 2 C 3 I 3 C C 3 C 3 Ag 2, 2 3 C C 3 C 3 hexan-2-amine,,-trimethylhexan-2-aminium iodide (a quaternary ammonium ion) form quaternary ammonium ion by overalkylation with C3I iodide is exchanged for hydroxide by adding Ag2 the ammonium hydroxide undergoes β-elimination to give least substituted alkene (offmann elimination) 1-hexene rganic Chemistry II (CM 224) Slide 28
22 Zaitsev)ule)vs.)offmann)ule 2 1. C 3 I 2. Ag 2, 2, heat regioselectivity: least substituted alkene 2 S 4, 2, heat 2 S 4, 2, heat regioselectivity: most substituted alkene stereoselectivity: trans alkene (E) Elimination of alcohols is reversible: thermodynamic control (most stable products obtained) offmann elimination is not reversible: kinetic control (most stable transition state path) rganic Chemistry II (CM 224) Slide 29
23 a-onalizing)egioselec-vity 3 C 3 1 C 3 (C 3 ) 3 3 C C 3 X 3 C C 3 1 (C 3 ) 3 3 higher energy (C 3 ) 3 1 C 3 3 (C 3 ) 3 3 C C 3 (C 3 ) 3 lower energy emember: E2 must orient β- and leaving group anti For elimination at β-c-3, larger steric repulsion between methyl group and -(C3)3 which is as big as tert-butyl rganic Chemistry II (CM 224) Slide 30
24 WiPg)vs.)offmann Wittig + 3 C PPh 3 Br offmann 2 Wittig reactions have largely replaced offmann since they are high yielding and completely regioselective rganic Chemistry II (CM 224) Slide 31
25 CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie Experiment'42 Aldol*Condensa8on
26 Mixed)Aldol + C 3 2 X 2 3-nitrochalcone C 3 (E)-1,3-diphenylbut-2-en-1-one (A) Procedure Dissolve aldehyde in 95% Et Add acetophenone to aldehyde Add 2 drops a soln Stir 5 min Add ice water Filter product (wash with cold Me to dry in < 5 min) ecrystallize all from ml Me Questions Why is chalcone not formed as the major product? What alternative non-aqueous conditions would ensure 3- nitrochalcaone was the major product? What I evidence will suggest we ve obtained our product? rganic Chemistry II (CM 224) Slide 33
27 CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie ext'lecture.'.'. Diazonium*Salts*(Sandmeyer):*24.8 Ch.*25:*Carbohydrates
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