L-Glutamic acid dibenzyl ester → dibenzyl N-[N-(2-hexadecanoyloxyhexadecanoyl)-L-valyl]-L-glutamate

HRID 236489Notes

Reaction equation

[C:1]([O:18][CH:19]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:20]([NH:22][C@H:23]([C:27]([OH:29])=O)[CH:24]([CH3:26])[CH3:25])=[O:21])(=[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].[NH2:44][C@H:45]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[CH2:46][CH2:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49]>>[C:1]([O:18][CH:19]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:20]([NH:22][C@H:23]([C:27]([NH:44][C@H:45]([C:58]([O:60][CH2:61][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)=[O:59])[CH2:46][CH2:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])=[O:29])[CH:24]([CH3:25])[CH3:26])=[O:21])(=[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 54524559N-[2-(Hexadecanoyloxy)hexadecanoyl]-L-valine

Product 1

HCID 54284467dibenzyl N-[N-(2-hexadecanoyloxyhexadecanoyl)-L-valyl]-L-glutamateYield 90.4%

Procedure

Starting from N-(2-hexadecanoyloxyhexadecanoyl)-L-valine (2.4 g) prepared by the method of Preparation B-2 and dibenzyl L-glutamate (1.26 g), dibenzyl N-[N-(2-hexadecanoyloxyhexadecanoyl)-L-valyl]-L-glutamate (3.2 g) was obtained as crystals according to a similar manner to that of Example 2. M.p. 65° C.

Sources & evidence

ORD record: ord-de28c504e8254c2ca7ddeea630eaa863
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643990

Reaction notes

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