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

HRID 75778Notes

Reaction equation

HRID 75778 reaction equation
C[O:2][C:3](=[O:33])[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][CH:30]=[CH:29][CH:28]=3)=[O:25])=[CH:19][CH:18]=2)[CH:13]=1)=[O:11])[CH:5]([CH3:8])[CH2:6][CH3:7].[K+].[Br-]>>[CH3:8][CH:5]([CH2:6][CH3:7])[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:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:25])=[CH:19][CH:18]=2)[CH:13]=1)=[O:11])[C:3]([OH:33])=[O:2]

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 46181356(S)-3-methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-pentanoic acid methyl ester

Product 1

HCID 46181357(S)-3-Methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-pentanoic acidYield 66.5%

Procedure

The title compound was prepared from (S)-3-methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-pentanoic acid methyl ester as set forth in Example 8 and was obtained in 66.5% yield. Mass (ES+): 437 (M++1); IR (KBr): 3336, 3280, 1717, 1667 (br), 1599, 1542 (br); 1H NMR (DMSO-d6) δ: 0.84, 0.88 (2×d, 6H), 1.51-1.68 (m, 2H), 1.71-1.79 (m, 1H), 4.36 (m, 1H), 6.94 (t, 1H), 7.25 (t, 2H), 7.42 (d, 2H), 7.57 (d, 2H), 7.58 (s, 1H), 7.80 (d, 2H), 8.77 (br, 1H), 8.97 (br, 1H), 9.13 (d, 1H).

Workup

  1. customwas obtained in 66.5% yield

Sources & evidence

ORD record
ord-387b45d03ca741a09c0beb3887ddf4ad
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

Loading…