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

HRID 75792Notes

Reaction equation

HRID 75792 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])=[CH:13][CH:12]=2)[C:7]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:5])C.Cl.[CH3:35][O:36][C:37](=[O:43])[C@@H:38]([NH2:42])[CH:39]([CH3:41])[CH3:40]>>[CH3:35][O:36][C:37](=[O:43])[C@@H:38]([NH:42][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[O:19])=[CH:15][CH:16]=2)[C:7]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:5])[CH:39]([CH3:41])[CH3:40]

Participants

3

Reactant 2

HCID 111190Methyl valinate hydrochlorideHCID 673521533-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-4-phenyl-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 46181512(S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-4-phenyl-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl esterYield 88.7%

Procedure

The title compound was prepared from 3-{4-[3-(4-fluoro-phenyl)-ureido]-phenyl}-4-phenyl-isoxazole-5-carboxylic acid ethyl ester and (S)-2-amino-3-methyl-butyric acid methyl ester hydrochloride using the procedure as set forth in Example 5 and was obtained in 88.7% yield. Mass (ES+): 531 (M++1); 1H NMR (DMSO-d6) δ: 0.79 (m, 6H), 2.02 (m, 1H), 3.65 (s, 3H), 4.29 (m, 1H), 7.11 (t, 1H), 7.43-7.47 (m, 2H), 7.52 (m, 3H), 7.55 (d, 2H), 7.67 (d, 2H), 7.81 (m, 2H), 8.74 (s, 1H), 8.93 (s, 1H), 9.25 (d, 1H).

Workup

  1. customwas obtained in 88.7% yield

Sources & evidence

ORD record
ord-ae36ae63f82544c195a56c1069979b3a
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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