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

HRID 2380104Notes

Reaction equation

HRID 2380104 reaction equation
C(O[C:6]([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:7])(C)(C)C.[O:39]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]([NH:48][C@H:49](C(O)=O)[CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])[CH2:41][CH2:40]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>>[O:39]1[CH2:40][CH2:41][N:42]([CH2:45][C:46]([NH:48][C@H:49]([C:6]([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])([CH3:29])[CH3:28])[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])[CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])[CH2:43][CH2:44]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 14989089(2S, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamideHCID 15018012N-morpholinoacetyl-L-phenylalanine

Product 1

HCID 14989061(2S, 4S, 5S)-5-{N-[N-Morpholinoacetyl-L-phenylalanyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-methylhexanamideYield 77%

Procedure

A procedure similar to that described in Example 2 was repeated, except that 100 mg (0.18 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)], 58 mg (0.20 mmoles) of N-morpholinoacetyl-L-phenylalanine, 0.03 ml (0.20 mmoles) of diethyl cyanophosphate, and 0.08 ml (0.57 mmoles) of triethylamine were used, to obtain 101 mg (yield 77%) of the title compound as a white amorphous substance.

Sources & evidence

ORD record
ord-3e9467fd05eb4003959576ddde6b05b5
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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