(S)-Homo-beta-valine → HCID 66721044, compound

HRID 1639923Notes

Reaction equation

HRID 1639923 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O-])=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=2[Cl:24])=[CH:4][C:3]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].[NH2:32][C@H:33]([CH:38]([CH3:40])[CH3:39])[CH2:34][C:35]([OH:37])=[O:36]>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:32][C@H:33]([CH:38]([CH3:40])[CH3:39])[CH2:34][C:35]([OH:37])=[O:36])=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=2[Cl:24])=[CH:4][C:3]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 439734(S)-Homo-beta-valineHCID 86637363HCID 86637363, compound

Product 1

HCID 66721044HCID 66721044, compoundYield 130.2%

Procedure

According to the saponification/peptide coupling steps described in examples 1.7 and 9 respectively, starting from 385 mg (0.84 mmol) of 6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-chloro-5-methylphenyl)pyridine-2-carboxylate and 130 mg (1 mmol) of (3S)-3-amino-4-methylpentanoic acid (J. Org. Chem., 1999, 6411-6417), we obtain 333 mg of (3S)-3-({[6-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-(2-chloro-5-methylphenyl)pyridin-2-yl]carbonyl}amino)-4-methylpentanoic acid hydrochloride in the form of white powder.

Sources & evidence

ORD record
ord-fdae6d9f0af44ed6b241336060b9defa
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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