L-Phenylalanine → N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-valyl]-L-phenylalanine

HRID 1903540

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][C@H:24]([C:28]([OH:30])=O)[CH:25]([CH3:27])[CH3:26])=[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:55]([OH:57])=[O:56])[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>>[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][C@H:24]([C:28]([NH:46][C@H:47]([C:55]([OH:57])=[O:56])[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:30])[CH:25]([CH3:26])[CH3:27])=[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 6140L-Phenylalanine

HCID 53729937N-[3-(Hexadecanoyloxy)octadecanoyl]-L-valine

Product 1

HCID 53905210N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-valyl]-L-phenylalanineYield 73.1%

Procedure

Starting from N-(3-hexadecanoyloxyoctadecanoyl)-L-valine (1 g) prepared by the method of Example 28 and L-phenylalanine (777 mg), N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-valyl]-L-phenylalanine (900 mg) was obtained as powders according to a similar manner to that of Example 29.

Sources & evidence

ORD record: ord-49329c6501d84cc3862aa0c4cb3a5396
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04436726

Linked notes

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