Hydrogen Peroxide → 4-(2'-Carboxy-2'-methylpropylsulfinyl)phenyl 2-Phenylbutyrate

HRID 249539Notes

Reaction equation

HRID 249539 reaction equation
[C:1]1([CH:7]([CH2:25][CH3:26])[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][CH2:18][C:19]([C:22]([OH:24])=[O:23])([CH3:21])[CH3:20])=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:27]O>C(O)(=O)C>[C:1]1([CH:7]([CH2:25][CH3:26])[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH2:18][C:19]([C:22]([OH:24])=[O:23])([CH3:20])[CH3:21])=[O:27])=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 183690134-(2'-Carboxy-2'-methylpropylmercapto)phenyl 2-phenylbutyrate

Product 1

HCID 183689684-(2'-Carboxy-2'-methylpropylsulfinyl)phenyl 2-Phenylbutyrate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(2'-carboxy-2'-methylpropylmercapto)phenyl 2-phenylbutyrate (745 mg, 2 mmol) in 1 mL of glacial acetic acid was added 0.25 mL of 30% H2O2. Additional 0.25 mL aliquots of 30% H2O2 were added at one-half hour intervals until TLC indicated complete consumption of the starting material. The reaction was quenched with 20 mL of H2O, extracted with Et2O (2×25 mL), dried over anhydrous MgSO4 and evaporated to give the sulfoxide containing a residual amount of acetic acid. The residue was suspended in 20 mL of H2O, the mixture was shell frozen and lyophilized to give 506 mg (65%) of the pure product sulfoxide. 1H NMR (CDCl3) δ1.00 (t, 3H, J=7.4 Hz), 1.42 (s, 3H), 1.54 (s, 3H), 1.85-1.99 (m, 1H), 2.16-2.31 (m, 1H), 3.07 (s, 2H), 3.72 (t, 1H, J=7.6 Hz), 7.17 (d, 2H, J=8.7 Hz), 7.32-7.40 (ArH, 5H), 7.70 (d, 2H, J=8.7 Hz), 11.17 (br s, --OH); 13C NMR (CDCl3) δ 11.83, 24.54, 25.71, 26.39, 41.73, 53.26, 68.81, 122.75, 125.60, 127.73, 128.10, 128.98, 138.30, 141.34, 153.11, 172.49, 180.33.

Workup

  1. customconsumption of the starting material
  2. customThe reaction was quenched with 20 mL of H2O
  3. extractionextracted with Et2O (2×25 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ada7e97e444b48cf810bf892c8548b4b
Source dataset
uspto-grants-1993_05
Patent number
US05214191

Reaction notes

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