Palmitoyl chloride → dibenzyl N-(N-hexadecanoyl-L-valyl)-L-glutamate

HRID 236501Notes

Reaction equation

C(OC([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.[C:39](Cl)(=[O:55])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>>[C:39]([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])[CH:10]([CH3:11])[CH3:12])(=[O:55])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

Participants

Reactant 2

HCID 8206Palmitoyl chloride

HCID 54081958dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)glutamate

Product 1

HCID 53989800dibenzyl N-(N-hexadecanoyl-L-valyl)-L-glutamateYield 63.4%

Procedure

Starting from dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)-L-glutamate (1 g) and hexadecanoyl chloride (620 mg), dibenzyl N-(N-hexadecanoyl-L-valyl)-L-glutamate (800 mg) was obtained as crystals according to a similar manner to that of Example 24.

Sources & evidence

ORD record: ord-9536b881da8e425a9b09543e05f20054
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643990

Reaction notes

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