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

HRID 75783

Reaction equation

HRID 75783 reaction equation
[CH:1]1([NH:7][C:8](=[O:24])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([C:21](O)=[O:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:26][O:27][C:28](=[O:35])[C@@H:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32].[K+].[Br-]>>[CH3:26][O:27][C:28](=[O:35])[C@@H:29]([NH:34][C:21]([C:19]1[O:18][N:17]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:24])=[CH:15][CH:14]=2)[CH:20]=1)=[O:22])[CH2:30][CH:31]([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 2723695Leucine methyl ester hydrochlorideHCID 673528493-[4-(3-Cyclohexyl-ureido)-phenyl]-isoxazole-5-carboxylic acid

Product 1

HCID 46181431(S)-2-({3-[4-(3-cyclohexyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-4-methyl-pentanoic acid methyl esterYield 67.9%

Procedure

The title compound was prepared from 3-[4-(3-cyclohexyl-ureido)-phenyl]-isoxazole-5-carboxylic acid and (S)-2-amino-4-methyl-pentanoic acid methyl ester hydrochloride as set forth in Example 5 and was obtained in 67.9% yield. Mass (ES+): 457 (M++1); IR (KBr): 3328, 2931, 1752 (br), 1655 (br), 1542 (br); 1H NMR (DMSO-d6) δ: 0.87, 0.91 (2×d, 6H), 1.14-1.81 (5×m, 13H), 3.47 (br, 1H), 3.65 (s, 3H), 4.49 (m, 1H), 6.17 (d, 1H), 7.52 (d, 2H), 7.59 (s, 1H), 7.77 (d, 2H), 8.59 (s, 1H), 8.96 (br, 1H), 9.32 (d, 1H).

Workup

  1. customwas obtained in 67.9% yield

Sources & evidence

ORD record
ord-d03dcc7e69b545bdb51623c25862a315
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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