Methyl valinate hydrochloride → (S)-3-Methyl-2-({4-phenyl-3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acid methyl ester

HRID 75790Notes

Reaction equation

HRID 75790 reaction equation
[C:1]1([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])=[CH:17][CH:16]=3)=[N:9][O:10][C:11]=2[C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:32][O:33][C:34](=[O:40])[C@@H:35]([NH2:39])[CH:36]([CH3:38])[CH3:37]>>[CH3:32][O:33][C:34](=[O:40])[C@@H:35]([NH:39][C:12]([C:11]1[O:10][N:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:23])=[CH:17][CH:16]=2)[C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:14])[CH:36]([CH3:38])[CH3:37]

Participants

3

Reactant 2

HCID 111190Methyl valinate hydrochlorideHCID 67353390HCID 67353390, compound

Product 1

HCID 46181508(S)-3-Methyl-2-({4-phenyl-3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acid methyl esterYield 76.5%

Procedure

The title compound was prepared from 4-phenyl-3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carboxylic acid and (S)-2-amino-3-methyl-butyric acid methyl ester hydrochloride using the procedure as set forth in Example 5 and was obtained in 76.5% yield. 1H NMR (DMSO-d6) δ: 0.79 (m, 6H), 2.01 (m, 1H), 4.30 (m, 1H), 6.96 (t, 1H), 7.27 (t, 2H), 7.44 (d, 2H), 7.53 (m, 3H), 7.56 (d, 2H), 7.67 (d, 2H), 7:81 (m, 2H), 8.72 (s, 1H), 8.93 (s, 1H), 9.25 (d, 1H); Mass (ES+), 513 (M++1).

Workup

  1. customwas obtained in 76.5% yield

Sources & evidence

ORD record
ord-632bedbf111b475ca425a21d93e5ce73
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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