Triethylamine → (2S, 4S, 5S)-5-[N-(N-Morpholinoacetyl-L-phenylalanyl)-3-(4-thiazolyl)-L-alanyl]amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyloctanamide

HRID 2380111Notes

Reaction equation

HRID 2380111 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:32][CH:33]([CH3:35])[CH3:34])[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:36]1[CH2:41][CH2:40][N:39]([CH2:42][C:43]([NH:45][C@H:46](C(O)=O)[CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:44])[CH2:38][CH2:37]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>>[O:36]1[CH2:37][CH2:38][N:39]([CH2:42][C:43]([NH:45][C@H:46]([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])[CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:44])[CH2:40][CH2:41]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 14989088(2S, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyloctanamideHCID 15018012N-morpholinoacetyl-L-phenylalanine

Product 1

HCID 14989073(2S, 4S, 5S)-5-[N-(N-Morpholinoacetyl-L-phenylalanyl)-3-(4-thiazolyl)-L-alanyl]amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyloctanamideYield 79.5%

Procedure

A procedure similar to that described in Example 2 was repeated, except that 100 mg (0.19 mmoles) of (2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-4-hydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-N-methyloctanamide [prepared as described in Example 16(a)], 62 mg (0.21 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 104 mg (yield 78%) of the title compound as a white amorphous substance.

Sources & evidence

ORD record
ord-4b03d6107d974b65a0e1ec1288ff1920
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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