m-Chloroperbenzoic acid → HCID 57294913, compound

HRID 863355Notes

Reaction equation

HRID 863355 reaction equation
C(=O)([O-])[OH:2].[Na+].[CH2:6]([N:8]([CH2:47][CH3:48])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:18]1[C@H:19]([CH3:46])[C@@H:20]2[C@@H:37]([C@H:38]([O:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH3:39])[C:36](=[O:45])[N:21]2[C:22]=1[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])=[O:10])[CH3:7].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH2:47]([N:8]([CH2:6][CH3:7])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([C:18]1[C@H:19]([CH3:46])[C@@H:20]2[C@@H:37]([C@H:38]([O:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH3:39])[C:36](=[O:45])[N:21]2[C:22]=1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)=[O:24])=[O:2])=[O:10])[CH3:48]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 99607884-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

Product 1

HCID 57294913HCID 57294913, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

122 mg (1.45 mmol) of sodium hydrogencarbonate were added to 6 ml of a methylene chloride solution containing 304 mg (0.486 mmol) of 4-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 34). The mixture was then placed in an ice bath while 105 mg (0.487 mmol) of m-chloroperbenzoic acid (80% purity) were added, with stirring. The reaction mixture was stirred for 1 hour at the same temperature, after which it was diluted with methylene chloride and washed with an ice-cooled dilute aqueous solution of sodium hydrogencarbonate. The solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 25 g of silica gel. Elution with a 2:1 by volume mixture of ethyl acetate and hexane afforded 260 mg (yield 83%) of the title compound as a foam-like solid.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred for 1 hour at the same temperature
  3. washwashed with an ice-
  4. temperaturecooled dilute aqueous solution of sodium hydrogencarbonate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through 25 g of silica gel
  7. washElution with a 2:1
  8. additionby volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4514992643a34392926abb7caf05fe7a
Source dataset
uspto-grants-1998_02
Patent number
US05719275

Reaction notes

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