1-Chloroethyl chloroformate → HCID 69951033, compound

HRID 1699663Notes

Reaction equation

HRID 1699663 reaction equation
C([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[NH:10][C:9]21[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]2)C1C=CC=CC=1.ClC(OC(Cl)C)=O>C(Cl)Cl>[C:11]1(=[O:18])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9]2([CH2:23][CH2:22][CH2:21][CH2:20][NH:19]2)[NH:10]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 86757787HCID 86757787, compound

Product 1

HCID 69951033HCID 69951033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of intermediate compound IV (1.0 eq) and Protol Sponge (Aldrich, 1.0 eq) in CH2Cl2 under N2 was cooled to 10° C. A solution of 1-chloroethyl chloroformate (1.5 eq) in CH2Cl2 was added in a dropwise fashion over 30 min, and the reaction was stirred for 2 h while warming to room temperature. The reaction mixture was then subjected to chromatography by vacuum filtration (SiO2:CH2Cl2/Acetone). The resulting white solid was then suspended in MeOH and refluxed for 30 min. The solvent was then removed in vacuo to afford the desired product as the hydrochloride salt (70% yield).

Workup

  1. filtrationThe reaction mixture was then subjected to chromatography by vacuum filtration (SiO2:CH2Cl2/Acetone)
  2. temperaturerefluxed for 30 min
  3. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-53a5e80415c74eaabeeb52fca374d84a
Source dataset
uspto-grants-2002_02
Patent number
US06348472B1

Reaction notes

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