Triethylamine → (2S, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N,N-dimethylhexanamide

HRID 2380107Notes

Reaction equation

HRID 2380107 reaction equation
C(OC([NH:8][C@@H:9]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C@@H:10]([OH:22])[CH2:11][C@@H:12]([C:18]([OH:21])([CH3:20])[CH3:19])[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=O)(C)(C)C.C(OC(N[C@@H](CC1CCCCC1)[C@@H](O)C[C@@H](C(O)(C)C)C(NC)=O)=O)(C)(C)C.[C:58]([O:62][C:63]([NH:65][C@H:66]([C:73]([OH:75])=O)[CH2:67][C:68]1[N:69]=[CH:70][S:71][CH:72]=1)=[O:64])([CH3:61])([CH3:60])[CH3:59].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>>[C:58]([O:62][C:63]([NH:65][C@H:66]([C:73]([NH:8][C@@H:9]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C@@H:10]([OH:22])[CH2:11][C@@H:12]([C:18]([OH:21])([CH3:20])[CH3:19])[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[O:75])[CH2:67][C:68]1[N:69]=[CH:70][S:71][CH:72]=1)=[O:64])([CH3:59])([CH3:60])[CH3:61]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 2734486(S)-2-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acidHCID 14989081(2S, 4S, 5S)-5-(t-butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamideHCID 14989083(2S, 4S, 5S)-5-(t-butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N,N-dimethylhexanamide

Product 1

HCID 86748259(2S, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N,N-dimethylhexanamideYield 71.9%

Procedure

A procedure similar to that described in Example 9(a) was repeated, except that 152 mg of (2S, 4S, 5S)- 5-(t-butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N,N-dimethylhexanamide (prepared as described in Preparation 25) were used instead of the (2S, 4S, 5S)-5-(t-butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamide, and that 109 mg (0.4 mmoles) of N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanine, 0.23 ml (1.66 mmoles) of triethylamine, and 0.064 ml (0.4 mmoles) of diethyl cyanophosphate were also used, to obtain 150 mg of the title compound as a white amorphous substance.

Sources & evidence

ORD record
ord-49aaa943204442b99cc3b434a320806b
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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