4-Nitrophenyl chloroformate → HCID 57559940, compound

HRID 1724194Notes

Reaction equation

HRID 1724194 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[CH:14]([OH:16])[CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:34]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:33](=[O:34])([O:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)[O:16][CH:14]([CH3:15])[C:13](=[C:11]1[CH2:12][N:9]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[CH2:10]1)[C:17]1[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=1

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 57559932HCID 57559932, compound

Product 1

HCID 57559940HCID 57559940, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 420 mg (0.91 mmol) of 1-{1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-1-(3,5-difluorophenyl)propan-2-ol, prepared according to the procedures of Example 35, and 222 mg (1.82 mmol) of 4-dimethylaminopyridine in 10 mL of methylene chloride was added 276 mg (1.37 mmol) of 4-nitrophenyl chloroformate and was stirred for 4 h at rt. The reaction mixture was concentrated and the residue was purified by silica gel chromatography with hexanes/ethyl acetate=12:1 to afford the title compound as a white solid. Mass Spectrum: m/e=627 (M+1 35Cl, 35Cl) and 629 (M+1 35Cl, 37Cl).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography with hexanes/ethyl acetate=12:1

Sources & evidence

ORD record
ord-b5ee6f421acc445e857fa76caedd2373
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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