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

HRID 75789Notes

Reaction equation

C[O:2][C:3](=[O:34])[C@@H:4]([NH:9][C:10]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[O:25])=[CH:19][CH:18]=2)[CH:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7].[K+].[Br-]>>[F:33][C:30]1[CH:29]=[CH:28][C:27]([NH:26][C:24](=[O:25])[NH:23][C:20]2[CH:19]=[CH:18][C:17]([C:14]3[CH:13]=[C:12]([C:10]([NH:9][C@@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:34])=[O:2])=[O:11])[O:16][N:15]=3)=[CH:22][CH:21]=2)=[CH:32][CH:31]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 46181435(S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester

Product 1

HCID 46181436(S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-4-methyl-pentanoic acidYield 58%

Procedure

The title compound was prepared from (S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester using the procedure as set forth in Example 8 and was obtained in 58% yield. Mass (ES+): 455 (M++1); IR (KBr): 3336 (br), 2962, 1724, 1664 (br), 1600, 1543 (br), 1510 (br); 1H NMR (DMSO-d6) δ: 0.87, 0.91 (2×d, 6H), 1.57-1.68 (m, 2H), 1.74-1.82 (m, 1H), 4.41 (m, 1H), 7.12 (t, 2H), 7.46 (m, 2H), 7.59 (d, 2H), 7.61 (s, 1H), 7.82 (d, 2H), 8.80 (s, 1H), 8.97 (s, 1H), 9.17 (d, 1H).

Workup

customwas obtained in 58% yield

Sources & evidence

ORD record: ord-ffdd51714c574821863888078ff9a846
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835428B2

Reaction notes

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