Hydrogen chloride-ethyl acetate → N-Palmitoylglycine

HRID 926804Notes

Reaction equation

HRID 926804 reaction equation
[NH:1]([C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:11])[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].Cl.CCOC(C)=O>>[NH:1]([C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:11])[CH2:2][C:3]([OH:5])=[O:4]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131735029N-palmitoyl-Gly-OtBu

Product 1

HCID 151008N-PalmitoylglycineYield 77.2%

Procedure

To N-palmitoyl-Gly-OtBu (17.4 g, 47.1 mmol), 4M HCl/AcOEt (118 ml, 0.471 mmol) was added and the whole was stirred at room temperature for 1 hour. After concentration under reduced pressure, the residue was washed with hexane to give 11.4 g (77%) of a target compound as colorless powder.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-f397d5a210184964879788c1c5e14fc5
Source dataset
uspto-grants-2016_03
Patent number
US09289496B2

Reaction notes

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