Triethylamine → (2S, 4S, 5S)-5-{N-[2(R)-(1-Naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamide

HRID 2380103Notes

Reaction equation

HRID 2380103 reaction equation
C(OC([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C@@H:20]([OH:31])[CH2:21][C@@H:22]([C:27]([OH:30])([CH3:29])[CH3:28])[C:23]([NH:25][CH3:26])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=O)(C)(C)C.[C:39]1([CH2:49][C@H:50]([CH2:54][C:55]([N:57]2[CH2:62][CH2:61][O:60][CH2:59][CH2:58]2)=[O:56])[C:51](O)=[O:52])[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][CH:40]=1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>>[C:39]1([CH2:49][C@H:50]([CH2:54][C:55]([N:57]2[CH2:58][CH2:59][O:60][CH2:61][CH2:62]2)=[O:56])[C:51]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:32][CH:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]2)[C@@H:20]([OH:31])[CH2:21][C@@H:22]([C:27]([OH:30])([CH3:28])[CH3:29])[C:23]([NH:25][CH3:26])=[O:24])=[O:17])[CH2:10][C:11]2[N:12]=[CH:13][S:14][CH:15]=2)=[O:52])[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 13913945(2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acidHCID 14989089(2S, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamide

Product 1

HCID 14989060(2S, 4S, 5S)-5-{N-[2(R)-(1-Naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamideYield 80.1%

Procedure

A procedure similar to that described in Example 2 was repeated, except that 100 mg (0.17 mmoles) of (2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamide [prepared as described in Example 9(a)], 71 mg (0.22 mmoles) of 2(R)-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionic acid, 0.03 ml (0.20 mmoles) of diethyl cyanophosphate, and 0.08 ml (0.57 mmoles) of triethylamine were used, obtain 104 mg (yield 75%) of the title compound as an amorphous substance.

Sources & evidence

ORD record
ord-cd9fd90f711c406da05ec8a35a5deb40
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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