L-Phenylalanine → N-[N-[3-(9-octadecenoyloxy)-11-eicosenoyl]glycyl]-L-phenylalanine

HRID 1903551Notes

Reaction equation

HRID 1903551 reaction equation
[C:1]([O:20][CH:21]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH:37]=[CH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:22][C:23]([NH:25][CH2:26][C:27]([OH:29])=O)=[O:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:47][C@H:48]([C:56]([OH:58])=[O:57])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[C:1]([O:20][CH:21]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH:37]=[CH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:22][C:23]([NH:25][CH2:26][C:27]([NH:47][C@H:48]([C:56]([OH:58])=[O:57])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:29])=[O:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 6140L-PhenylalanineHCID 54315012N-[3-(9-octadecenoyloxy)-11-eicosenoyl]glycine

Product 1

HCID 54244061N-[N-[3-(9-octadecenoyloxy)-11-eicosenoyl]glycyl]-L-phenylalanineYield 73.3%

Procedure

Starting from N-[3-(9-octadecenoyloxy)-11-eicosenoyl]glycine (2.0 g) prepared by the method described in Example 40 and L-phenylalanine (2.64 g), N-[N-[3-(9-octadecenoyloxy)-11-eicosenoyl]glycyl]-L-phenylalanine (1.8 g) was obtained as powders according to a similar manner to that of Example 29.

Workup

  1. customprepared by the method

Sources & evidence

ORD record
ord-f3350414392749dca85efff04888d826
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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