Triethylamine → (2S, 4S, 5S)-5-{N-[2(R)-(1-Naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyloctanamide

HRID 2380110Notes

Reaction equation

HRID 2380110 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:16]([NH:18][CH:19]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH:20]([OH:31])[CH2:21][CH: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:7])(C)(C)C.[C:36]1([CH2:46][C@H:47]([CH2:51][C:52]([N:54]2[CH2:59][CH2:58][O:57][CH2:56][CH2:55]2)=[O:53])C(O)=O)[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>>[C:36]1([CH2:46][C@H:47]([CH2:51][C:52]([N:54]2[CH2:59][CH2:58][O:57][CH2:56][CH2:55]2)=[O:53])[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:32][CH:33]([CH3:34])[CH3:35])[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:7])[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 13913945(2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acidHCID 542871065-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyl octanamide

Product 1

HCID 14989072(2S, 4S, 5S)-5-{N-[2(R)-(1-Naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyloctanamideYield 94%

Procedure

4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyl octanamide [prepared as described in Example 16(a)], 119 mg (0.36 mmoles) of 2(R)-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionic acid, 0.06 ml (0.40 mmoles) of diethyl cyanophosphate, and 0.14 ml (1.00 mmoles) of triethylamine were used, to obtain 205 mg (yield 94%) of the title compound as a white amorphous substance.

Sources & evidence

ORD record
ord-83f33f1830364db5ace5ea185ffdfa34
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

Loading…