2-Hexadecanoyloxyhexadecanoic acid → N-[N-(2-hexadecanoyloxyhexadecanoyl)-beta-alanyl]-L-threonine

HRID 1903546Notes

Reaction equation

HRID 1903546 reaction equation
[C:1]([O:18][CH:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]([OH:22])=O)(=[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].[NH2:37][CH2:38][CH2:39][C:40]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[C@@H:44]([CH3:46])[OH:45])=[O:41]>>[C:1]([O:18][CH:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]([NH:37][CH2:38][CH2:39][C:40]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[C@@H:44]([CH3:46])[OH:45])=[O:41])=[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

3

Reactant 2

HCID 133718622-Hexadecanoyloxyhexadecanoic acidHCID 18649800beta-alanyl-L-threonine

Product 1

HCID 54508912N-[N-(2-hexadecanoyloxyhexadecanoyl)-beta-alanyl]-L-threonineYield 86%

Procedure

Starting from 2-hexadecanoyloxyhexadecanoic acid (200 mg) prepared by the method described in Preparation 7 and N-β-alanyl-L-threonine (190 mg), N-[N-(2-hexadecanoyloxyhexadecanoyl)-β-alanyl]-L-threonine (230 mg) was obtained as crystals according to a similar manner to that of Example 6.

Workup

  1. customprepared by the method

Sources & evidence

ORD record
ord-5f6ac18f0e9d41e8a129740fe91e55a4
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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