Oxalic Acid → benzyl N-(2-oxoethyl)carbamate

HRID 865393

Reaction equation

HRID 865393 reaction equation
C1COCC1.C(O)(=O)C(O)=O.C[O:13][CH:14](OC)[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O>[CH2:20]([O:19][C:17]([NH:16][CH2:15][CH:14]=[O:13])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 8028TetrahydrofuranHCID 10800009Benzyl (2,2-dimethoxyethyl)carbamate

Product 1

HCID 11217768benzyl N-(2-oxoethyl)carbamateYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 80 ml THF, 40 ml water, and 800 mg oxalic acid was added 9.6 g (40 mmol) of N-benzyloxycarbonyl aminoacetaldehyde dimethyl acetal, and refluxed for 4 days. The THF was removed under reduced pressure and the remaining solution was extracted with ether (3×100 ml), the ether fractions were combined and dried over anhydrous sodium sulfate. The ether was removed under reduced pressure and the remaining solution was purified by flash chromatography (hexane and ethyl acetate 3:1 then 1:1) to yield 3.88 g, 50% yield.

Workup

  1. temperaturerefluxed for 4 days
  2. customThe THF was removed under reduced pressure
  3. extractionthe remaining solution was extracted with ether (3×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ether was removed under reduced pressure
  6. customthe remaining solution was purified by flash chromatography (hexane and ethyl acetate 3:1
  7. custom1:1) to yield 3.88 g, 50% yield

Sources & evidence

ORD record
ord-d8425ece4df34afe83c8f585afdadcbe
Source dataset
uspto-grants-1996_10
Patent number
US05565585

Linked notes

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