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

HRID 75788Notes

Reaction equation

HRID 75788 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:36])[C@@H:30]([NH2:35])[CH2:31][CH:32]([CH3:34])[CH3:33].[K+].[Br-]>>[CH3:27][O:28][C:29](=[O:36])[C@@H:30]([NH:35][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])[CH2:31][CH:32]([CH3:34])[CH3:33]

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 2723695Leucine methyl ester hydrochlorideHCID 673531173-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carboxylic acid

Product 1

HCID 46181435(S)-2-[(3-{4-[3-(4-Fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-4-methyl-pentanoic acid methyl esterYield 69.5%

Procedure

The title compound was prepared from 3-{4-[3-(4-fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carboxylic acid and (S)-2-amino-4-methyl-pentanoic acid methyl ester hydrochloride using the procedure as set forth in Example 5 and was obtained in 69.5% yield. Mass (ES+): 469 (M++1); IR (KBr): 3312 (br), 2960, 1743, 1665 (br), 1612, 1597, 1542 (br), 1508; 1H NMR (DMSO-d6) δ: 0.85, 0.90 (2×d, 6H), 1.59 (m, 2H), 1.79 (m, 1H), 3.64 (s, 3H), 4.47 (m, 1H), 7.11 (t, 1H), 7.45 (m, 2H), 7.58 (d, 2H), 7.60 (s, 1H), 7.82 (d, 2H), 8.78 (sr, 1H), 8.95 (s, 1H), 9.32 (d, 1H).

Workup

  1. customwas obtained in 69.5% yield

Sources & evidence

ORD record
ord-f4b270031997442e97b50287f077d48a
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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