Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoate → tert-Butyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrate

HRID 1251887Notes

Reaction equation

HRID 1251887 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[C:20]([CH:24]=2)[C:21](O)=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[C:34]([O:38][C:39](=[O:46])[C@H:40]([CH2:42][CH2:43][S:44][CH3:45])[NH2:41])([CH3:37])([CH3:36])[CH3:35]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[C:20]([CH:24]=2)[C:21]([NH:41][C@@H:40]([CH2:42][CH2:43][S:44][CH3:45])[C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:46])=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7010638Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 183244905-(1-(4-Fluorophenyl)-2-(imidazol-1-yl)ethoxy)-2-(4-fluorophenethyl)benzoic acid

Product 1

HCID 57034377tert-Butyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrateYield 80%

Procedure

The title compound was prepared in 80% yield from 5-(1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy)-2-(4-fluorophenethyl)benzoic acid and L-methionine tert-butyl ester by a similar method to that used for Example 34. 1H NMR (DMSO-d6, 300 MHz) δ: 1.38 (9H,s); 1.88-2.0 (2H,m); 2.02 (3H,d); 2.62-2.75 (2H,m); 2.75-2.9 (2H,m); 4.32-4.42 (1H, m); 4.68 (2H,d); 5.83 (1H,m); 6.79-6.83 (2H,md); 6.95-7.1 (3H,m); 7.1-7.28 (4H,m); 7.45-7.52 (2H,dd); 7.61 (1H,s); 7.68 (1H,s); 8.62 (1H,t); 9.08 (1H,s). MS (ES+) m/z 636.4 (MH+); Anal.calculated for C35H39F2N3O4S.2.7H2O C, 61.4; H, 6.5; N, 6.1%; Found: C, 61.1; H, 6.2; N, 5.7%.

Sources & evidence

ORD record
ord-f0bf445e7d494daaa354fdd03c8d44d4
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…