Chlorosuccinimide → HCID 59494031, compound

HRID 872021Notes

Reaction equation

HRID 872021 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH:9]1([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]1>C(#N)C>[Cl:1][C:26]1[CH:25]=[C:24]([O:27][CH3:28])[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:22][C:21]=1[CH2:20][N:12]([CH:9]1[CH2:11][CH2:10]1)[C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67545206HCID 67545206, compound

Product 1

HCID 59494031HCID 59494031, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

N-Chlorosuccinimide (110 mg) was added to a solution of tert-butyl cyclopropyl[4-methoxy-3-(3-methoxypropoxy)benzyl]carbamate (300 mg) in acetonitrile (5.0 ml) under ice cooling and the mixture was stirred at room temperature for an hour and at 75° C. for 5 hours. The reaction mixture was concentrated in vacuo and the resulted residue was purified with a NH-silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1 to 3/1) to give tert-butyl [2-chloro-4-methoxy-5-(3-methoxypropoxy)benzyl]cyclopropylcarbamate (265 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulted residue was purified with a NH-silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1 to 3/1)

Sources & evidence

ORD record
ord-8e0a0cce42604e1d86afd004e104a90c
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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