N-(tert-butoxycarbonyl)-L-aspartic acid → (S)-tert-Butyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

HRID 613218Notes

Reaction equation

HRID 613218 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:14](=[O:15])[O:16][C:11](=[O:13])[CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 99718N-(tert-butoxycarbonyl)-L-aspartic acid

Product 1

HCID 13657126(S)-tert-Butyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 23.3 g N-t-butyloxycarbonyl-L-aspartic acid in 150 mL of tetrahydrofuran was added portionwise 20.6 g of N,N-dicyclohexyl-carbodiimide at 0° C. and overnight at room temperature. The precipitated dicyclohexyl urea was filtered off and all solvent was evaporated under reduced pressure. The oily residue was crystallized from acetone/hexane to give 18.24 g of anydride as white needles.

Workup

  1. customovernight
  2. customat room temperature
  3. filtrationThe precipitated dicyclohexyl urea was filtered off
  4. customall solvent was evaporated under reduced pressure
  5. customThe oily residue was crystallized from acetone/hexane
  6. customto give 18.24 g of anydride as white needles

Sources & evidence

ORD record
ord-671e327625df43ec844fd6ebc60ff142
Source dataset
uspto-grants-1999_12
Patent number
US06008058

Reaction notes

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