23138-53-6 → HCID 67095556, compound

HRID 909044Notes

Reaction equation

HRID 909044 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([C:26]#[N:27])[C@H:12]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:11][NH:10][C@@H:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[Cl:25])=[C:4]([F:28])[CH:3]=1.[CH3:29][O:30][C:31](=[O:41])[C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1>C(Cl)Cl>[CH3:29][O:30][C:31](=[O:41])[C:32]1[CH:33]=[CH:34][C:35]([NH:38][C:39]([N:10]2[CH2:11][C@@H:12]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C@@:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=3[F:28])([C:26]#[N:27])[C@H:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[Cl:25])=[O:40])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 28045423138-53-6HCID 58222887HCID 58222887, compound

Product 1

HCID 67095556HCID 67095556, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of rac-4-{[(2S,3S,4S)-3-(4-chloro-2-fluoro-phenyl)-2-(2,3-dichloro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (88.0 mg, 0.20 mmol) and 4-isocyanato-benzoic acid methyl ester (Aldrich, 42.5 mg, 0.22 mmol) in CH2Cl2 (2 mL) was stirred at rt for 1 h. The reaction mixture was then concentrated and purified by flash column to give rac-4-{[(2S,3S,4S)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,3-dichloro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-benzoic acid methyl ester (98.6 mg, 79.9%) which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-4b9c948dfa334a729e43c28e3dfa1291
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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