3-(3-Cyanophenyl)-2-(pyrrolidin-2-yl)-propionic acid methyl ester → 2-[1-[3-(Tert-butyloxycarbonylaminomethyl)biphenyl-4-carbonyl]-pyrrolidin-2-yl]-3-(3-cyanophenyl)-propionic acid methyl ester

HRID 901323Notes

Reaction equation

HRID 901323 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[CH:14][C:15]=1[C:16](O)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][O:26][C:27](=[O:43])[CH:28]([CH:38]1[CH2:42][CH2:41][CH2:40][NH:39]1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=1>>[CH3:25][O:26][C:27](=[O:43])[CH:28]([CH:38]1[CH2:42][CH2:41][CH2:40][N:39]1[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][C:10]=1[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:17])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=1

Participants

3

Reactant 2

HCID 692529693-(3-Cyanophenyl)-2-(pyrrolidin-2-yl)-propionic acid methyl esterHCID 692550623-(tert-Butyloxycarbonylaminomethyl)biphenyl-4-carboxylic acid

Product 1

HCID 692549922-[1-[3-(Tert-butyloxycarbonylaminomethyl)biphenyl-4-carbonyl]-pyrrolidin-2-yl]-3-(3-cyanophenyl)-propionic acid methyl esterYield 80%

Procedure

3-(tert-Butyloxycarbonylaminomethyl)biphenyl-4-carboxylic acid (1.15 g, 3.5 mmol) and 3-(3-cyanophenyl)-2-(pyrrolidin-2-yl)-propionic acid methyl ester (0.91 g, 3.5 mmol) are coupled as described in EXAMPLE 1B to give the title compound (1.22 g, 2.8 mmol). 1H NMR (CDCl3, 300 MHz) □ 7.63-7.25(m, 12H), 4.85-4.70(two m, 1H), 4.48(m, 1H), 4.38(br.s, 2H), 3.80-3.71(m, 1H), 3.68, 3.62(two s, 3H), 3.63-3.40(m, 2H), 3.21-3.10(m, 1H), 2.90-2.78(m, 1H), 2.20-2.05(m, 1H), 2.02-1.65(m, 3H), 1.45(s, 9H).

Sources & evidence

ORD record
ord-b763e57f9ebe41bd8bfd5cff50ba5aac
Source dataset
uspto-grants-2008_04
Patent number
US07361663B2

Reaction notes

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