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

HRID 2380113Notes

Reaction equation

HRID 2380113 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.[O:41]1[CH2:46][CH2:45][N:44]([CH2:47][C:48]([NH:50][C@H:51](C(O)=O)[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:49])[CH2:43][CH2:42]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>>[O:41]1[CH2:42][CH2:43][N:44]([CH2:47][C:48]([NH:50][C@H:51]([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])[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:49])[CH2:45][CH2:46]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 14989091(2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-ethyl-1-hydroxypropyl)-N-methylhexanamideHCID 15018012N-morpholinoacetyl-L-phenylalanine

Product 1

HCID 14989065(2S, 4S, 5S)-5-[N-(N-Morpholinoacetyl-L-phenylalanyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-(1-ethyl-1-hydroxypropyl)-N-methylhexanamideYield 80%

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-ethyl-1-hydroxypropyl)-N-methylhexanamide [prepared as described in Example 18(a)], 55 mg (0.19 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 103 mg (yield 79%) of the title compound as a white amorphous substance.

Sources & evidence

ORD record
ord-f5c910f023444571b469774cd7f6a715
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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