HCID 58466015, compound → HCID 58466005, compound

HRID 2198060Notes

Reaction equation

HRID 2198060 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([N:13]2[CH2:17][CH2:16][CH:15]([S:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH:25]OS([O-])=O.[K+].S(OOS([O-])(=O)=O)([O-])(=O)=O>CC(C)=O>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[C:5]([N:13]2[CH2:17][CH2:16][CH:15]([S:18]([CH2:19][C:20]([OH:22])=[O:21])=[O:25])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 58466015HCID 58466015, compoundHCID 86658343HCID 86658343, compound

Product 1

HCID 58466005HCID 58466005, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of optically resolved tR1 (AS, 300 mg) of ({1-[3,5-bis(trifluoromethyl)phenyl]pyrrolidin-3-yl}sulfanyl)acetic acid obtained in Example 10 in acetone (10 mL) was added aqueous solution (5 ml) of Oxone-persulfate compound (500 mg) at 0° C., and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to give the title compound (291 mg, yield 93%) as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-15f74e85fd75437a8eaad822ec1960f6
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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