Hydrochloric Acid → (2S,4S)-1-(tert-butoxycarbonyl)-4-(8-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidine-2-carboxylic acid

HRID 1675437Notes

Reaction equation

HRID 1675437 reaction equation
[Cl:1][C:2]1[C:3]([O:38][CH3:39])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[N:13]1)[CH:8]=[C:7]2[O:21][C@@H:22]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:24]([C:34]([O:36]C)=[O:35])[CH2:23]1.[Li+].[OH-].O.Cl>C1COCC1>[C:30]([O:29][C:27]([N:25]1[CH2:26][C@@H:22]([O:21][C:7]2[C:6]3[C:11](=[C:2]([Cl:1])[C:3]([O:38][CH3:39])=[CH:4][CH:5]=3)[N:10]=[C:9]([N:12]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[N:13]3)[CH:8]=2)[CH2:23][C@H:24]1[C:34]([OH:36])=[O:35])=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 66650753HCID 66650753, compound

Product 1

HCID 57816711(2S,4S)-1-(tert-butoxycarbonyl)-4-(8-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidine-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 112 (650 mg, 1.13 mmol) in THF (12 mL) was added LiOH (82 mg, 3.41 mmol) and water. The reaction mixture was stirred at room temperature for 16 hrs and was acidified with 1N HCl to pH 5-6. Aqueous layer was extracted with EtOAc. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 113 as a pink solid in 95% yield.

Workup

  1. extractionAqueous layer was extracted with EtOAc
  2. dry with materialOrganics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-033d4e0756fb40aea40a89ec23f0a7cf
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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