Isopropyl Acetate → (2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid

HRID 1697560Notes

Reaction equation

HRID 1697560 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][N:6]1[C:20]1[N:21]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[N:22]=[C:23]([CH3:25])[CH:24]=1)=[O:4].O.[OH-].[Li+].C(OC(C)=O)(C)C>C1COCC1.O>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([C@H:8]1[CH2:7][N:6]([C:20]2[N:21]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][CH:27]=3)[N:22]=[C:23]([CH3:25])[CH:24]=2)[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 7915Isopropyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 67278056(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770810(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic acid methyl ester (27 mg, 51 umol) was dissolved in THF (0.2 ml). A solution of lithium hydroxide monohydrate (3 mg, 72 umol) in water (0.2 ml) was added and the mixture was stirred at ambient temperature for 14 h. Ice water/0.1 N aqueous HCl solution 1/1 and iPrOAc were added and the layers were separated. The aqueous layer was extracted one more time with iPrOAc, the combined organic layers were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound compound (26 mg, 51 umol; quant.) as a yellow oil which was used in the next step without further purification. MS (ESI): m/z=514.3 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted one more time with iPrOAc
  3. washthe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7bfe4f3b9d01413683335481fefdea65
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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