Leucine methyl ester hydrochloride → (S)-4-Methyl-2-({4-phenyl-3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-pentanoic acid methyl ester

HRID 75791Notes

Reaction equation

HRID 75791 reaction equation
[C:1]1([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])=[CH:17][CH:16]=3)=[N:9][O:10][C:11]=2[C:12](O)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:32][O:33][C:34](=[O:41])[C@@H:35]([NH2:40])[CH2:36][CH:37]([CH3:39])[CH3:38]>>[CH3:32][O:33][C:34](=[O:41])[C@@H:35]([NH:40][C:12]([C:11]1[O:10][N:9]=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])=[CH:19][CH:20]=2)[C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:13])[CH2:36][CH:37]([CH3:39])[CH3:38]

Participants

3

Reactant 2

HCID 2723695Leucine methyl ester hydrochlorideHCID 67353390HCID 67353390, compound

Product 1

HCID 46181510(S)-4-Methyl-2-({4-phenyl-3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-pentanoic acid methyl esterYield 83%

Procedure

The title compound was prepared from 4-phenyl-3-[4-(3-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 83% yield. Mass (ES−): 525 (M−−1); 1H NMR (DMSO-d6) δ: 0.75, 0.81 (2×d, 6H), 1.35-1.58 (m, 3H), 3.66 (s, 3H), 4.49 (m, 1H), 6.96 (t, 1H), 7.27 (t, 2H), 7.44 (d, 2H), 7.54 (m, 3H), 7.56 (d, 2H), 7.66 (d, 2H), 7.82 (m, 2H), 8.72 (br, 1H), 8.95 (br, 1H), 9.31 (d, 1H).

Workup

  1. customwas obtained in 83% yield

Sources & evidence

ORD record
ord-aebcd8e88c9b491cb62106c2cac919f1
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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