Acetic Anhydride → (R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

HRID 1401872Notes

Reaction equation

HRID 1401872 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@H:9]([CH2:20][OH:21])[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>ClCCl>[C:1]([NH:8][C@H:9]([CH2:20][OH:21])[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10655432(2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

Product 1

HCID 10889901(R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (4 grams) was added to the solution of (R)-2-amino-N-benzyl-3-hydroxypropanamide compound of formula-10 (6 grams) in dichloromethane (60 ml) at 10-15° C. The reaction mixture was stirred for 3 hours and reaction mixture quenched with water. Both the organic and aqueous layers were separated. The organic layer was washed with aqueous sodium bicarbonate solution followed by water. The organic layer was distilled off completely under reduced pressure to get the title compound.

Workup

  1. customreaction mixture
  2. customquenched with water
  3. customBoth the organic and aqueous layers were separated
  4. washThe organic layer was washed with aqueous sodium bicarbonate solution
  5. distillationThe organic layer was distilled off completely under reduced pressure

Sources & evidence

ORD record
ord-640d1bb3e03a4823857e2befc408b994
Source dataset
uspto-grants-2014_12
Patent number
US08907132B2

Reaction notes

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