m-Chloroperbenzoic acid → HCID 67732365, compound

HRID 863767Notes

Reaction equation

HRID 863767 reaction equation
[CH2:1]([S:8][CH2:9][CH:10]1[O:16][CH:15]2[N:12]([C:13](=[O:17])[CH2:14]2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([S:8]([CH2:9][CH:10]1[O:16][CH:15]2[N:12]([C:13](=[O:17])[CH2:14]2)[CH2:11]1)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67732423HCID 67732423, compound

Product 1

HCID 67732365HCID 67732365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of (3RS, 5SR)-3-Benzylthiomethyl-4-oxa-1-azabicyclo[3,2,0] heptan-7-one (926 mg) in Dichloromethane (10 ml), the solution of m-Chloroperbenzoic acid (72%, 755 mg) in Dichloromethane (30 ml) was added dropwise under ice-cooling and stirred at same condition for 1 hr. The reaction mixture was poured into aqueous Sodium hydrogen carbonate, extracted with Chloroform, and dried over Sodium sulfate. The reaction mixture was purified by column (Ethyl acetate+Acetone 5:1). Yield: 570 mg (58%). m.p. 80.5°~94.5° C. NMR (CDCl3): 2.63-3.39 (5H, m), 4.03-4.15 (3H, m), 4.59-4.77 (1H, m), 7.26-7.40 (5H, m). IR (Nujol), cm-1 : 2940, 1706, 1494.

Workup

  1. temperaturecooling
  2. extractionextracted with Chloroform
  3. dry with materialdried over Sodium sulfate
  4. customThe reaction mixture was purified by column (Ethyl acetate+Acetone 5:1)

Sources & evidence

ORD record
ord-caa0fcc83ae94b8a838bd5430925b6fb
Source dataset
uspto-grants-1996_10
Patent number
US05561126

Reaction notes

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