Acetic Anhydride → (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

HRID 2118800Notes

Reaction equation

HRID 2118800 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2723942N-(Benzyloxycarbonyl)aspartic acid

Product 1

HCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamateYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 16.0 g N-benzyloxycarbonyl-L-aspartic acid (Z-Asp) in 24 ml toluene, was added 7.7 g of acetic anhydride, and the reaction was continued at room temperature for six hours to form N-benzyloxycarbonyl-L-aspartic anhydride (Z-Asp O).

Sources & evidence

ORD record
ord-64df422fbe084e798452d5bdbd16193f
Source dataset
uspto-grants-1987_07
Patent number
US04680403

Reaction notes

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