m-Chloroperbenzoic acid → HCID 13132545, compound

HRID 355010Notes

Reaction equation

HRID 355010 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[OH:12][C@@H:13]([C@H:15]1[C:21](=[O:22])[N:20]2[C@@H:16]1[CH2:17][C:18]([CH2:36][S:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=1)=[O:42])=[C:19]2[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])[CH3:14]>C(Cl)Cl.CS(C)=O>[OH:12][C@@H:13]([C@H:15]1[C:21](=[O:22])[N:20]2[C@@H:16]1[CH2:17][C:18]([CH2:36][S:37]([CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][C:48]([N+:51]([O-:53])=[O:52])=[CH:49][CH:50]=1)=[O:42])=[O:9])=[C:19]2[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])[CH3:14]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13132543HCID 13132543, compound

Product 1

HCID 13132545HCID 13132545, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 22 mg of m-chloroperbenzoic acid in 2 ml of methylene chloride was added dropwise to 60 mg of p-nitrobenzyl (5R,6S)-6-[1-(R)-hydroxyethyl]-3-(2-p-nitrobenzyloxycarbonylaminoethyl)thiomethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (53), prepared as described in step (g) of Example 6, in 3 ml of methylene chloride, whilst cooling with ice-water. When the addition was complete, the reaction mixture was stirred at 0°-5° C. for 30 minutes. The resulting mixture containing precipitated material was diluted with 100 ml of ethyl acetate and then the solution was washed successively with a 5% w/v aqueous solution of sodium hydrogen sulphite (once), a saturated aqueous solution of sodium bicarbonate (twice) and a saturated aqueous solution of sodium chloride (three times). The solution was then dried over sodium sulphate, after which the solvents were evaporated under reduced pressure at room temperature, to give a solid substance. This crude substance was dissolved in dimethyl sulphoxide and then reprecipitated by the addition of benzene, to give 55 mg of the title compound as an amorphous powder.

Workup

  1. customprepared
  2. additionWhen the addition
  3. additionThe resulting mixture containing
  4. customprecipitated material
  5. additionwas diluted with 100 ml of ethyl acetate
  6. washthe solution was washed successively with a 5% w/v aqueous solution of sodium hydrogen sulphite (once), a saturated aqueous solution of sodium bicarbonate (twice) and a saturated aqueous solution of sodium chloride (three times)
  7. dry with materialThe solution was then dried over sodium sulphate
  8. customafter which the solvents were evaporated under reduced pressure at room temperature
  9. customto give a solid substance
  10. customreprecipitated by the addition of benzene

Sources & evidence

ORD record
ord-6aae59531f8d43558ad304eb8ce43fcd
Source dataset
uspto-grants-1983_03
Patent number
US04377591

Reaction notes

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