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

HRID 902968Notes

Reaction equation

HRID 902968 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)carbamate

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 complete, the mixture was stirred at ambient temperature for 4 h. The organic layer was separated, washed with brine (2×100 mL) and concentrated to provide the title compound. MS (DCl/NH3): m/z 240 (M+1)+, 257 (M+18)+.

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-15db506d78ad4b979541e502917613ab
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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