Benzyl chloroformate → Ethyl 2-(((benzyloxy)carbonyl)(methyl)amino)acetate

HRID 1896889Notes

Reaction equation

HRID 1896889 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(OCC)(=O)C>[CH2:18]([O:17][C:15]([N:7]([CH3:6])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 95849Glycine, N-methyl-, ethyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 58562640Ethyl 2-(((benzyloxy)carbonyl)(methyl)amino)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A rapidly stirred mixture of ethyl acetate and saturated aqueous sodium bicarbonate containing commercially available commercially available 2 ethyl 2-(methylamino)acetate (1.91 g, 12.4 mmol, HCl salt) was cooled to 0° C. and treated dropwise with benzyl chloroformate (4.10 mL, 12.3 mmol). After stirring overnight warming to room temperature, the aqueous layer was removed and the organic layer concentrated in vacuo. Purification of the residue by flash chromatography (silica gel, DCM) yielded the product.

Workup

  1. temperaturewarming to room temperature
  2. customthe aqueous layer was removed
  3. concentrationthe organic layer concentrated in vacuo
  4. customPurification of the residue by flash chromatography (silica gel, DCM)
  5. customyielded the product

Sources & evidence

ORD record
ord-2a43bfa4b3fe4955a69a587b02dd8137
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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