(S)-2-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acid → (2R, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide

HRID 1768841Notes

Reaction equation

HRID 1768841 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C@@H:10]([OH:20])[CH2:11][C@@H:12]([CH3:19])[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14])=[O:7])(C)(C)C.[C:28]([O:32][C:33]([NH:35][C@H:36](C(O)=O)[CH2:37][C:38]1[N:39]=[CH:40][S:41][CH:42]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([NH:35][C@H:36]([C:6]([NH:8][C@@H:9]([CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[C@@H:10]([OH:20])[CH2:11][C@@H:12]([CH3:19])[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14])=[O:7])[CH2:37][C:38]1[N:39]=[CH:40][S:41][CH:42]=1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 2734486(S)-2-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acidHCID 57031843(2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide

Product 1

HCID 15045768(2R, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamideYield 78%

Procedure

The procedure described in Example 5(a) was repeated, but using 280 mg (0.728 mmole) of (2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide (prepared as described in Preparation 18) and 204 mg (0.75 mmole) of N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanine, to afford 306 mg of the title compound as colorless crystals, melting at 182°-184° C.

Sources & evidence

ORD record
ord-1596f344af094f9ba9d1b7310a8d3a7c
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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