L-Glutamic acid dibenzyl ester → dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-5-aminopentanoyl]-L-glutamate

HRID 236495Notes

Reaction equation

[C:1]([O:18][CH:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=O)=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:46][C@H:47]([C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:61])[CH2:48][CH2:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51]>>[C:1]([O:18][CH:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:46][C@H:47]([C:60]([O:62][CH2:63][C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)=[O:61])[CH2:48][CH2:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])=[O:30])=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Reactant 2

HCID 3037947L-Glutamic acid dibenzyl ester

HCID 133718635-(3-Hexadecanoyloxyoctadecanoyl)aminovaleric acid

Product 1

HCID 18606669dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-5-aminopentanoyl]-L-glutamateYield 79.7%

Procedure

Starting from N-(3-hexadecanoyloxyoctadecanoyl)-5-aminopentanoic acid (1.27 g) prepared by the method of Preparation B-6 and dibenzyl L-glutamate (0.65 g), dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-5-aminopentanoyl]-L-glutamate (1.5 g) was obtained as crystal according to a similar manner to that of Example 2.

Sources & evidence

ORD record: ord-09808bbfc13041a89eaba08b4e5c20ec
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643990

Reaction notes

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