Methyl 2-isocyanatobenzoate → HCID 51356120, compound

HRID 909066Notes

Reaction equation

HRID 909066 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.[N:29]([C:32]1[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=1[C:34]([O:36][CH3:37])=[O:35])=[C:30]=[O:31]>C(Cl)Cl>[CH3:37][O:36][C:34](=[O:35])[C:33]1[CH:38]=[CH:39][CH:40]=[CH:41][C:32]=1[NH:29][C:30]([N:9]1[CH2:10][C@@H:11]([CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C@@:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[F:22])([C:13]#[N:14])[C@H:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:28])=[O:31]

Participants

4

Reactant 2

HCID 519494Methyl 2-isocyanatobenzoateHCID 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 51356120HCID 51356120, compoundYield 68.1%

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 (70.3 mg, 0.166 mmol) and methyl 2-isocyanatobenzoate (Aldrich, 150.7 mg, 0.851 mmol) in CH2Cl2 (9 mL) was stirred at rt for 18 hrs. The reaction mixture was then concentrated and purified by flash column to give rac-2-{[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-benzoic acid methyl ester (67.9 mg, 68.1%). HRMS (ES+) m/z Calcd for C31H29Cl2F2N3O3+Na [(M+Na): 622.1446; Found: 622.1449.

Workup

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

Sources & evidence

ORD record
ord-367fb60cf6ae4d0caa4056efe98faa24
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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