Triacontanoic acid → dibenzyl N-(N-triacontanoyl-L-valyl)-L-glutamate

HRID 236503Notes

Reaction equation

[C:1]([OH:32])(=O)[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(OC([NH:40][C@H:41]([C:45]([NH:47][C@H:48]([C:61]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62])[CH2:49][CH2:50][C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])=[O:46])[CH:42]([CH3:44])[CH3:43])=O)(C)(C)C>>[C:1]([NH:40][C@H:41]([C:45]([NH:47][C@H:48]([C:61]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62])[CH2:49][CH2:50][C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])=[O:46])[CH:42]([CH3:43])[CH3:44])(=[O:32])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Reactant 2

HCID 10471Triacontanoic acid

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

Product 1

HCID 54014072dibenzyl N-(N-triacontanoyl-L-valyl)-L-glutamateYield 50%

Procedure

Starting from triacontanoic acid (452 mg) and dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)-L-glutamate (526 mg), dibenzyl N-(N-triacontanoyl-L-valyl)-L-glutamate (430 mg) was obtained as powder according to a similar manner to that of Example 28.

Sources & evidence

ORD record: ord-aa5ec83584744ae8b5c520be6f8790c3
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643990

Reaction notes

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