Serine, glycyl- → N-[N-(3-hexanoyloxyoctanoyl)glycyl]-L-serine

HRID 1903530Notes

Reaction equation

HRID 1903530 reaction equation
[C:1]([O:8][CH:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10][C:11]([O:13]C(C)(C)C)=O)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:23][CH2:24][C:25]([NH:27][C@H:28]([C:31]([OH:33])=[O:32])[CH2:29][OH:30])=[O:26]>>[C:1]([O:8][CH:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10][C:11]([NH:23][CH2:24][C:25]([NH:27][C@H:28]([C:31]([OH:33])=[O:32])[CH2:29][OH:30])=[O:26])=[O:13])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 73086Serine, glycyl-HCID 20467294Tert-butyl 3-hexanoyloxyoctanoate

Product 1

HCID 54101773N-[N-(3-hexanoyloxyoctanoyl)glycyl]-L-serineYield 52.3%

Procedure

Starting from tert-butyl 3-hexanoyloxyoctanoate (157 mg) prepared by the method described in Preparation 5 and N-glycyl-L-serine (243 mg), N-[N-(3-hexanoyloxyoctanoyl)glycyl]-L-serine (105 mg) was obtained as an oil according to similar manner to that of Example 1.

Workup

  1. customprepared by the method

Sources & evidence

ORD record
ord-08e9c19e8a8c46bc9d04aea42f3f080d
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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