m-Chloroperbenzoic acid → HCID 86739902, compound

HRID 2413440Notes

Reaction equation

HRID 2413440 reaction equation
[CH:1]([O:14][C:15]([CH2:17][C:18]([NH:20][C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[C:29]1[S:33][C:32]([NH:34][C:35](=[O:38])[CH2:36][Cl:37])=[N:31][CH:30]=1)[CH:24]([S:39][C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([Cl:47])[CH:41]=1)[C:23]2=[O:48])=[O:19])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:57])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]([O:14][C:15]([CH2:17][C:18]([NH:20][C:21]1[N:22]2[CH:25]([S:26](=[O:57])[CH2:27][C:28]=1[C:29]1[S:33][C:32]([NH:34][C:35](=[O:38])[CH2:36][Cl:37])=[N:31][CH:30]=1)[CH:24]([S:39][C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([Cl:47])[CH:41]=1)[C:23]2=[O:48])=[O:19])=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86739903HCID 86739903, compound

Product 1

HCID 86739902HCID 86739902, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-benzhydryloxycarbonyl-3-(2-chloroacetamido-thiazol-5-yl)-7-(3,4-dichlorophenylthio)-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2 g) in methylene chloride (50 cc) is cooled to 0° C. and treated with an 85% strength solution of meta-chloroperbenzoic acid (0.45 g) in methylene chloride (10 cc). After 30 minutes at a temperature of between 0° and 5° C., the reaction mixture is diluted with methylene chloride (100 cc) and a saturated sodium bicarbonate solution (100 cc) is added. The solid which precipitates is filtered off and taken up in methylene chloride (200 cc). The decanted organic phase is added to this solution, after having been washed with water (100 cc) and then with a saturated sodium chloride solution (100 cc) and dried over sodium sulphate, and the mixture is then concentrated under reduced pressure to a residual volume of 10 cc. The solid is filtered off and washed with ethyl acetate (20 cc) and then with ethyl ether (20 cc). 2-Benzhydryloxycarbonyl-3-(2-chloroacetamido-thiazol-5-yl)-7-(3,4-dichlorophenylthio)-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (1.48 g) is obtained in the form of a cream solid.

Workup

  1. customThe solid which precipitates
  2. filtrationis filtered off
  3. additionThe decanted organic phase is added to this solution
  4. washafter having been washed with water (100 cc)
  5. dry with materialwith a saturated sodium chloride solution (100 cc) and dried over sodium sulphate
  6. concentrationthe mixture is then concentrated under reduced pressure to a residual volume of 10 cc
  7. filtrationThe solid is filtered off
  8. washwashed with ethyl acetate (20 cc)

Sources & evidence

ORD record
ord-12b10377461e4098b38c8f8921bc7197
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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