m-Chloroperbenzoic acid → HCID 59683600, compound

HRID 2389673Notes

Reaction equation

HRID 2389673 reaction equation
[Cl:1][C:2]1[C:3]2[C:45]([F:46])=[CH:44][CH:43]=[C:42]([F:47])[C:4]=2[S:5][C:6]=1[C:7]([N:9]([CH2:25][C:26]1[CH:27]=[C:28]([C:34]2[CH:39]=[CH:38][C:37]([S:40][CH3:41])=[CH:36][CH:35]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1)=[O:8].C([O-])(O)=[O:49].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl.[O-]S([O-])=O.[Na+].[Na+]>[Cl:1][C:2]1[C:3]2[C:45]([F:46])=[CH:44][CH:43]=[C:42]([F:47])[C:4]=2[S:5][C:6]=1[C:7]([N:9]([CH2:25][C:26]1[CH:27]=[C:28]([C:34]2[CH:35]=[CH:36][C:37]([S:40]([CH3:41])=[O:49])=[CH:38][CH:39]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:10]1[CH2:11][CH2:12][CH:13]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:14][CH2:15]1)=[O:8]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59683524HCID 59683524, compound

Product 1

HCID 59683600HCID 59683600, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24437Sodium SulfiteSolvent

Procedure

A stirred suspension of methyl sulfide 209 (75 mg, 0.11 mmol) and NaHCO3 (46 mg, 0.55 mmol) in DCM (3 mL) at 0° C. is treated with a solution of m-chloroperbenzoic acid (20 mg, 0.12 mmol) in DCM (1 mL) dropwise over 2 minutes. After stirring 2 h at RT, the reaction is diluted with aqueous Na2SO3 (10 mL) and extracted into DCM (3×10 mL). The combined DCM phases are then dried (Na2SO4) and reduced in vacuo. The residue is purified by column chromatography (gradient elution—10-90% EtOAc in heptane with 0.5% triethylamine) to give the title compound.

Workup

  1. extractionextracted into DCM (3×10 mL)
  2. dry with materialThe combined DCM phases are then dried (Na2SO4)
  3. customThe residue is purified by column chromatography (gradient elution—10-90% EtOAc in heptane with 0.5% triethylamine)

Sources & evidence

ORD record
ord-e5b725f2f9e94e89b2a9715c0f6190ab
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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