Lithium Hydroxide → HCID 67095371, compound

HRID 909045Notes

Reaction equation

HRID 909045 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][C@@H:16]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@@:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[F:32])([C:23]#[N:24])[C@H:14]2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=2[Cl:40])=[O:12])=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1.CO>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C@@:15]2([C:23]#[N:24])[C@H:16]([CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:17][N:13]([C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:41])=[O:2])=[CH:5][CH:6]=3)=[O:12])[C@@H:14]2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=2[Cl:40])=[C:26]([F:32])[CH:27]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67095556HCID 67095556, compound

Product 1

HCID 67095371HCID 67095371, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a mixture of 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 (85.0 mg, 0.14 mmol) in THF/MeOH (0.6 mL/0.2 mL) was added 4 N LiOH (0.2 mL), and the reaction mixture was stirred at rt for 2 hrs. The reaction mixture was concentrated and quenched with 2 NH2SO4, extracted with EtOAc, and washed with water, brine. The organic phase was separated, and dried over Na2SO4. The mixture was then concentrated 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 (54.3 mg, 65.4%). LC-MS (ES+) m/z Calcd for C30H27Cl3FN3O3+H [(M+H): 604; Found: 604.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customquenched with 2 NH2SO4
  3. extractionextracted with EtOAc
  4. washwashed with water, brine
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-cc8123ce27c645bea610c6cd60f62e79
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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