Chloromethyl chloroformate → HCID 18629466, compound

HRID 1060786Notes

Reaction equation

HRID 1060786 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].Cl.[NH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(C(C)C)CC)(C)C>ClCCl>[C:13]([O:12][C:10]([CH2:9][NH:8][C:2](=[O:3])[O:4][CH2:5][Cl:6])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 62754Chloromethyl chloroformateHCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 18629466HCID 18629466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chloromethyl chloroformate (1.69 g) in dichloromethane (5 ml) was added dropwise with stirring to an ice-cold solution of tert-butyl glycinate, hydrochloride (2.0 g) and diisopropylethylamine (3.7 g) in dichloromethane (20 ml). After stirring for a further 2 hours at room temperature, the mixture was extracted with ice-cold 0.5 M hydrochloric acid followed by water and aqueous sodium bicarbonate. Drying over magnesium sulfate and evaporation in vacuo gave the title compound as a colourless powder.

Workup

  1. extractionthe mixture was extracted with ice-cold 0.5 M hydrochloric acid
  2. dry with materialDrying over magnesium sulfate and evaporation in vacuo

Sources & evidence

ORD record
ord-cd5ced9e20664f7581ea4d9dea736144
Source dataset
uspto-grants-2003_02
Patent number
US06525077B2

Reaction notes

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