Potassium Bromide → (S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid

HRID 75787Notes

Reaction equation

C[O:2][C:3](=[O:33])[C@@H:4]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[CH:5]([CH3:7])[CH3:6].[K+].[Br-]>>[F:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:23](=[O:24])[NH:22][C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:12]=[C:11]([C:9]([NH:8][C@@H:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:33])=[O:2])=[O:10])[O:15][N:14]=3)=[CH:21][CH:20]=2)=[CH:31][CH:30]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

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

Product 1

HCID 46181434(S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acidYield 42%

Procedure

The title compound was prepared from (S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester using the procedure as set forth in Example 8 and was obtained in 42% yield. Mass (ES+): 441 (M++1); IR (KBr): 3316 (br), 1718, 1668 (br), 1612, 1600, 1552, 1510; 1H NMR (DMSO-d6) δ: 0.95 (2×d, 6H), 2.20 (m, 1H), 4.27 (q, 2H), 7.12 (t, 2H), 7.46 (m, 2H), 7.60 (d, 2H), 7.68 (s, 1H), 7.82 (d, 2H), 8.79 (s, 1H), 8.93 (s, 1H), 8.95 (d, 1H).

Workup

customwas obtained in 42% yield

Sources & evidence

ORD record: ord-503cc08264eb4142a78b123d73eac908
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835428B2

Reaction notes

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