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

HRID 1464209

Reaction equation

HRID 1464209 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>C(O)(=O)C>[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)carbamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

For example, N-benzyloxycarbonyl-L-aspartic acid is dissolved in a large excess of acetic anhydride, the acetic acid formed by the reaction and the excess acetic anhydride are distilled off under reduced pressure and the effect of any acetic acid remaining in the residue is removed by the addition of an organic solvent to give N-benzyloxycarbonyl-L-aspartic anhydride [J. Am. Chem. Soc., 81, 167-173 (1959)].

Workup

  1. distillationthe excess acetic anhydride are distilled off under reduced pressure
  2. customthe effect of any acetic acid remaining in the residue is removed by the addition of an organic solvent

Sources & evidence

ORD record
ord-0d00a997b1df4e23a14cef71c9b78832
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Linked notes

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