Benzyl chloroformate → Benzyl (2,2-dimethoxyethyl)carbamate

HRID 393789Notes

Reaction equation

HRID 393789 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH2:16].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH:16][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10800009Benzyl (2,2-dimethoxyethyl)carbamateYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzyl chloroformate (231.3 g, 1.3 mol) was added gradually to a mixture of aminoacetaldehyde dimethyl acetal (152.0 g, 1.3 mol) in toluene (750 mL) and aqueous NaOH (72.8 g, 1.82 mol; in 375 mL of water) at 10-20° C. After the addition was completed, the mixture was stirred at ambient temperature over 4 hours. The organic layer was separated, washed with brine (2×100 mL) and concentrated to provide the title compound as an oil (281.5 g, 90% yield). 1H NMR (CDCl4, 300 MHz) δ3.33 (t, J=6.0 Hz, 2H), 3.39 (s, 6H), 4.37 (t, J=6.0 Hz, 1H), 5.11 (s, 2H), 7.30 (m, 5H); MS (DCI/NH3) m/z 257 (M+NH4)+, 340 (M+H)+.

Workup

  1. additionAfter the addition
  2. customThe organic layer was separated
  3. washwashed with brine (2×100 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5e40aef5792743a088fb8073f7570544
Source dataset
uspto-grants-2004_10
Patent number
US06809105B2

Reaction notes

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