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

HRID 75777Notes

Reaction equation

HRID 75777 reaction equation
C[O:2][C:3](=[O:32])[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][CH:29]=[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-]>>[CH3:6][CH:5]([CH3:7])[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:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[C:3]([OH:32])=[O:2]

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 46181355(S)-3-Methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acid methyl ester

Product 1

HCID 67352473(S)-3-Methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acidYield 83%

Procedure

The title compound was prepared from (S)-3-methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acid methyl ester as set forth in Example 8 and was obtained in 83% yield. Mass (ES+): 423 (M++1); IR (KBr): 3347, 3317, 1708, 1671 (br), 1599, 1547 (br); 1H NMR (DMSO-d6) δ: 0.95 (2×d, 6H), 2.20 (m, 1H), 4.27 (q, 2H), 6.97 (t, 1H), 7.28 (t, 2H), 7.45 (d, 2H), 7.60 (d, 2H), 7.68 (s, 1H), 7.82 (d, 2H), 8.75 (s, 1H), 8.94 (d, 1H), 8.96 (d, 1H).

Workup

  1. customwas obtained in 83% yield

Sources & evidence

ORD record
ord-aede9bd60644496394e200b923ba6371
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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