Acetic Anhydride → HCID 178501452, compound

HRID 467273Notes

Reaction equation

HRID 467273 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])[NH2:6].C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C)C=O>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])[NH:6][C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178501501HCID 178501501, compound

Product 1

HCID 178501452HCID 178501452, compoundYield 148.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.0 gm (8.9 mMol) arginine methyl ester hydrochloride and 1.5 gm (14.8 mMol) triethylamine in dimethylformamide (150 ml) was added 776 mg (7.4 mMol) acetic anhydride dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 hour and then the volatiles removed under reduced pressure. The residue was purified using silica gel chromatography, eluting with ethyl acetate containing 0-50% methanol, to give N-acetyl arginine methyl ester as a crystalline solid (2.53 g).

Workup

  1. customthe volatiles removed under reduced pressure
  2. customThe residue was purified
  3. washeluting with ethyl acetate containing 0-50% methanol

Sources & evidence

ORD record
ord-53316deeb8224c9a8013e1533bf24544
Source dataset
uspto-grants-1992_10
Patent number
US05159081

Reaction notes

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