Formic Acid → Benzyl allyl(2-oxoethyl)carbamate

HRID 470209Notes

Reaction equation

HRID 470209 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16](OC)[O:17]C)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C(O)=O>O>[CH2:1]([N:4]([CH2:15][CH:16]=[O:17])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 11044136Benzyl allyl(2,2-dimethoxyethyl)carbamate

Product 1

HCID 57415664Benzyl allyl(2-oxoethyl)carbamateYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of benzyl N-allyl-N-(2,2-dimethoxyethyl)carbamate (30 g, 107 mmol) in formic acid (36.8 mL, 860 mmol) and water (4.84 mL) is stirred at room temperature overnight. The mixture is concentrated and diluted with hexanes/ethyl acetate (1:2) and water. The organic layer is separated, washed with brine solution until pH=6, and dried over sodium sulfate. The solvent is evaporated to give the title compound (25 g, 99%). ES/MS (m/e): 234 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with hexanes/ethyl acetate (1:2) and water
  3. customThe organic layer is separated
  4. washwashed with brine solution until pH=6
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-fdcd852a961e43c1ae6da7680fb2f90a
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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