N-(Benzyloxycarbonyl)aspartic acid → (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

HRID 356826

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

The above illustrated starting compound which is commercially available N-CBZ aspartic acid (205.7 g, 0.77 mol) was added to acetic anhydride (300 ml). This mixture was stirred at 75° C. for 4 hours. The excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure and the residue was recrystallised from hot dichloromethane. The product was collected by filtration, washed with hexane and dried at ambient temperature under reduced pressure to give a white fluffy solid.

Workup

distillationThe excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure
customthe residue was recrystallised from hot dichloromethane
filtrationThe product was collected by filtration
washwashed with hexane
customdried at ambient temperature under reduced pressure
customto give a white fluffy solid

Sources & evidence

ORD record: ord-f220232a1ce74980bd2c13304127a203
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840667

Linked notes

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