N-(2-Phenylacetyl)-L-aspartic acid → HCID 54081971, compound

HRID 979444Notes

Reaction equation

HRID 979444 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][C:13]([OH:15])=O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:16](=[O:17])[O:18][C:13](=[O:15])[CH2:12]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 13958181N-(2-Phenylacetyl)-L-aspartic acid

Product 1

HCID 54081971HCID 54081971, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

After cooling to 0°-5° C. and filtration the reaction mixture was dried to obtain N-phenyl acetylaspartic acid (120 g), 99.77% titer. 78 g of N-phenylacetyl aspartic acid were suspended in 80 ml of acetic anidride. The mixture was heated to 80° for 2 hours. 70 g of N-phenylacetyl aspartic anhydride were obtained after cooling and insolubilization with a solvent. 52 g of N-phenylacetyl aspartic anhydride suspended in 52 ml of glacial acetic acid and 100 ml of dichloroethane cooled to 10° C. were added with 200 ml of dichloroethane containing 40.2 g of phenylalanine methyl ester.

Workup

  1. temperatureThe mixture was heated to 80° for 2 hours

Sources & evidence

ORD record
ord-be6de01c373943389ba8ac02af7a9302
Source dataset
uspto-grants-1987_05
Patent number
US04668625

Reaction notes

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