Chloromethyl chloroformate → HCID 18629503, compound

HRID 1060784Notes

Reaction equation

HRID 1060784 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][NH2:18])=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C>ClCCl>[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:2](=[O:3])[O:4][CH2:5][Cl:6])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 62754Chloromethyl chloroformateHCID 81531DiisopropylethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 18629503HCID 18629503, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chloromethyl chloroformate (2.84 g) in dichloromethane (10 ml) was added dropwise with stirring to an ice-cold solution of 3-(N-tert-butoxycarbonylamino)-propylamine (3.49 g) and diisopropylethylamine (3.10 g) in dichloromethane (30 ml). After stirring for a further 3 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 colourless crystals.

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-269f5158bac8400b964c43d2d89f662e
Source dataset
uspto-grants-2003_02
Patent number
US06525077B2

Reaction notes

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