Acetic Anhydride → HCID 53972361, compound

HRID 1941304Notes

Reaction equation

HRID 1941304 reaction equation
[CH2:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11](=O)[NH2:12])=[O:7])[CH2:2][CH2:3][CH3:4].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH2:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11]#[N:12])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54542004HCID 54542004, compound

Product 1

HCID 53972361HCID 53972361, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-Butyloxycarbonyl-D-asparagine (25 g, 108 mmol) was dissolved in 200 mL pyridine and 14 mL acetic anhydride and the solution was allowed to stir overnight at room temperature. After most of the pyridine was removed under reduced pressure, ethyl acetate was added and the solution was washed with citric acid and brine, dried (MgSO4), and concentrated to give 21 g (91%) oily product. ES-MS: calcd M+1 215.0; found 215.0.

Workup

  1. customAfter most of the pyridine was removed under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe solution was washed with citric acid and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b4468a04ed5429b80bc3e70693ea699
Source dataset
uspto-grants-1997_12
Patent number
US05703092

Reaction notes

Loading…