4-Fluorophenyl isocyanate → HCID 51354453, compound

HRID 909069Notes

Reaction equation

HRID 909069 reaction equation
[Cl:1][C:2]1[C:3]([F:28])=[C:4]([CH:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][NH:9]2)[CH:5]=[CH:6][CH:7]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>C(Cl)Cl>[F:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([N:9]2[CH2:10][C@@H:11]([CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C@@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:8]2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:28])=[O:38])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 67095372rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile

Product 1

HCID 51354453HCID 51354453, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (43.1 mg, 0.102 mmol) and 4-fluorophenyl isocyanate (Aldrich, 71.0 mg, 0.512 mmol) in CH2Cl2 (5 mL) was stirred at rt for 24 hrs. The reaction mixture was then concentrated and purified by flash column to give (2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carboxylic acid (4-fluoro-phenyl)-amide (45.6 mg, 79.8%). HRMS (ES+) m/z Calcd for C29H26Cl2F3N3O+H [(M+H)+]: 560.1478; Found: 560.1479.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by flash column

Sources & evidence

ORD record
ord-c8954e70785445e0b8ebb7a1fafc3a0a
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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