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

HRID 75786Notes

Reaction equation

HRID 75786 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:25])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:21]=[C:20]([C:22](O)=[O:23])[O:19][N:18]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl.[CH3:27][O:28][C:29](=[O:35])[C@@H:30]([NH2:34])[CH:31]([CH3:33])[CH3:32].[K+].[Br-]>>[CH3:27][O:28][C:29](=[O:35])[C@@H:30]([NH:34][C:22]([C:20]1[O:19][N:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:25])=[CH:16][CH:15]=2)[CH:21]=1)=[O:23])[CH:31]([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 111190Methyl valinate hydrochlorideHCID 253877Potassium BromideHCID 673531173-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carboxylic acid

Product 1

HCID 46181433(S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl esterYield 84.2%

Procedure

The title compound was prepared from 3-{4-[3-(4-fluoro-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 84.2% yield. Mass (ES+): 455 (M++1); IR (KBr): 3310, 1742, 1672, 1553 (br), 1506, 1434; 1H NMR (DMSO-d6) δ: 0.92 (2×d, 6H), 2.18 (m, 1H), 3.65 (s, 3H), 4.29 (t, 1H), 7.11 (t, 2H), 7.59 (d, 2H), 7.66 (s, 1H), 7.82 (d, 2H), 8.77 (s, 1H), 8.94 (s, 1H), 9.16 (d, 1H).

Workup

  1. customwas obtained in 84.2% yield

Sources & evidence

ORD record
ord-8384e29ac5db4ed990643a851ed29c73
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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