L-Tryptophan → N-[N-(3-hexadecanoyloxyoctadecanoyl)glycyl]-L-tryptophan

HRID 1903553Notes

Reaction equation

[C:1]([O:18][CH:19]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:20][C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[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].[NH2:43][C@H:44]([C:55]([OH:57])=[O:56])[CH2:45][C:46]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1>>[C:1]([O:18][CH:19]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:20][C:21]([NH:23][CH2:24][C:25]([NH:43][C@H:44]([C:55]([OH:57])=[O:56])[CH2:45][C:46]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)=[O: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 6305L-Tryptophan

HCID 20216775N-[3-(Hexadecanoyloxy)octadecanoyl]glycine

Product 1

HCID 53838370N-[N-(3-hexadecanoyloxyoctadecanoyl)glycyl]-L-tryptophanYield 48.1%

Procedure

N-(3-hexadecanoyloxyoctadecanoyl)glycine (1.3 g) prepared by the method described in Example 27 and L-tryptophan (1.45 g), N-[N-(3-hexadecanoyloxyoctadecanoyl)glycyl]-L-tryptophan (820 mg) was obtained as powders according to a similar manner to that of Example 29.

Sources & evidence

ORD record: ord-238e99fe974940bca2d20251704072b5
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04436726

Reaction notes

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