Ethyl chloroformate → HCID 15392211, compound

HRID 362513Notes

Reaction equation

HRID 362513 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:34]=[CH:33][C:18]([NH:19][CH2:20][C:21]3[CH:30]=[C:29]4[C:24]([CH:25]=[CH:26][C:27]([C:31]#[N:32])=[CH:28]4)=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]4[C:29](=[CH:28][C:27]([C:31]#[N:32])=[CH:26][CH:25]=4)[CH:30]=3)[C:36](=[O:37])[O:38][CH2:39][CH3:40])=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 15392197HCID 15392197, compound

Product 1

HCID 15392211HCID 15392211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-[[4-[(1-t-Butoxycarbonyl-4-piperidyl)oxy]anilino]methyl]-2-naphthalenecarbonitrile obtained in Reference Example 2 (150 mg) was dissolved in 2 ml of dimethylformamide, 178 mg of ethyl chloroformate and 271 mg of potassium carbonate were added to the solution, and the mixture was stirred at room temperature for 3.5 hours. The reaction solution was evaporated, and the resulting residue was purified by silica gel column chromatography using ethyl acetate:hexane (2:8) as the eluent to give 169 mg of ethyl N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]carbamate.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c3a202dcd38409b9dd3a2816c9cef3f
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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