m-Chloroperbenzoic acid → HCID 17992736, compound

HRID 2118787Notes

Reaction equation

HRID 2118787 reaction equation
[C:1]([O:4][CH2:5][N:6]1[CH:9]([S:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]([CH2:20][CH2:21][CH3:22])[C:7]1=[O:23])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([O:4][CH2:5][N:6]1[CH:9]([S:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:32])[CH:8]([CH2:20][CH2:21][CH3:22])[C:7]1=[O:23])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19748777HCID 19748777, compound

Product 1

HCID 17992736HCID 17992736, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 46 mg (0.127 mmole) azetidinone from Step B in 4 ml CH2Cl2 and 4 ml saturated aqueous NaHCO3 was added 27 mg (0.127 mM) 80% m-chloroperbenzoic acid and the reaction mixture stirred vigorously 15 minutes. The phases were separated and the organic phase was dried over MgSO4, filtered and stripped to yield 57 mg crude product which was chromatographed on a 1000μ silica gel prep TLC plate in chloroform-ethyl acetate 4:1 to yield 15 mg (31%) of 1-acetoxymethyl-4-p-nitrophenylsulfinyl-3-n-propylazetidin-2-one.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customto yield 57 mg crude product which
  5. customwas chromatographed on a 1000μ silica gel prep TLC plate in chloroform-ethyl acetate 4:1

Sources & evidence

ORD record
ord-592dceb4b1b04bae86c3175a902f5046
Source dataset
uspto-grants-1987_07
Patent number
US04680391

Reaction notes

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