m-Chloroperbenzoic acid → HCID 58466005, compound

HRID 2198059Notes

Reaction equation

HRID 2198059 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.ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[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:33])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58466015HCID 58466015, compound

Product 1

HCID 58466005HCID 58466005, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ({1-[3,5-bis(trifluoromethyl)phenyl]pyrrolidin-3-yl}sulfanyl)acetic acid (500 mg) obtained in Example 1 and m-chloroperbenzoic acid (321 mg) in dichloromethane (25 mL) was stirred at room temperature for 2 hr. The solvent was evaporated, and the residue was purified by preparative HPLC (instrument: Gilson Inc., High throughput purification system; column: YMC Combiprep ODS-A, S-5 μm, 50×20 mm; solvent: SOLUTION A; 0.1% trifluoroacetic acid-containing water, SOLUTION B; 0.1% trifluoroacetic acid-containing acetonitrile; gradient cycle: 0.00 min (SOLUTION A/SOLUTION B=90/10), 1.00 min (SOLUTION A/SOLUTION B=90/10), 4.20 min (SOLUTION A/SOLUTION B=10/90), 5.40 min (SOLUTION A/SOLUTION B=10/90), 5.50 min (SOLUTION A/SOLUTION B=90/10), and 5.60 min (SOLUTION A/SOLUTION B=90/10); flow rate: 25 mL/min; detection method: UV 220 nm) to give the title compound (471 mg, yield 90%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (instrument: Gilson Inc., High throughput purification system; column: YMC Combiprep ODS-A, S-5 μm, 50×20 mm; solvent: SOLUTION A; 0.1% trifluoroacetic acid-containing water, SOLUTION B; 0.1% trifluoroacetic acid-containing acetonitrile; gradient cycle: 0.00 min (SOLUTION A/SOLUTION B=90/10), 1.00 min (SOLUTION A/SOLUTION B=90/10), 4.20 min (SOLUTION A/SOLUTION B=10/90), 5.40 min (SOLUTION A/SOLUTION B=10/90), 5.50 min (SOLUTION A/SOLUTION B=90/10), and 5.60 min (SOLUTION A/SOLUTION B=90/10); flow rate: 25 mL/min; detection method: UV 220 nm)

Sources & evidence

ORD record
ord-8598796327754a12834462b818888a08
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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