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-ethyl-1-hydroxypropyl)-N-methylhexanamide

HRID 2380112Notes

Reaction equation

HRID 2380112 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C@@H:20]([OH:33])[CH2:21][C@@H:22]([C:27]([CH2:31][CH3:32])([OH:30])[CH2:28][CH3:29])[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:41]1([CH2:51][C@H:52]([CH2:56][C:57]([N:59]2CCO[CH2:61][CH2:60]2)=[O:58])C(O)=O)[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1.P(C#N)([O:70][CH2:71][CH3:72])(OCC)=O.C(N(CC)CC)C>>[C:41]1([CH2:51][C@H:52]([CH2:56][C:57]([N:59]2[CH2:72][CH2:71][O:70][CH2:61][CH2:60]2)=[O:58])[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)[C@@H:20]([OH:33])[CH2:21][C@@H:22]([C:27]([CH2:28][CH3:29])([OH:30])[CH2:31][CH3:32])[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:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 13913945(2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acidHCID 14989091(2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-ethyl-1-hydroxypropyl)-N-methylhexanamide

Product 1

HCID 14989064(2S, 4S, 5S)-5-{N-[2(R)-(1-Naphthylmethyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-(1-ethyl-1-hydroxypropyl)-N-methylhexanamideYield 88%

Procedure

A procedure similar to that described in Example 2 was repeated, except that 120 mg (0.21 mmoles) of (2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-ethyl-1-hydroxypropyl)-N-methylhexanamide [prepared as described in Example 18(a)], 81 mg (0.25 mmoles) of 2(R)-(1-naphthylmethyl)-3-(morpholinocarbonyl)propionic acid, 0.04 ml (0.26 mmoles) of diethyl cyanophosphate, and 0.09 ml (0.65 mmoles) of triethylamine were used, to obtain 144 mg (yield 88%) of the title compound as a white amorphous substance.

Sources & evidence

ORD record
ord-8d88f7b0357e4b72a29159fb61ba7ee6
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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