m-Chloroperbenzoic acid → HCID 19819707, compound

HRID 1031120Notes

Reaction equation

HRID 1031120 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]([C:25]2[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=2)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:38].C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:32])=[O:38])=[CH:27][CH:26]=2)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate2×HCID 19819702HCID 19819702, compound

Product 1

HCID 19819707HCID 19819707, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.34 g (2.98 mmols) of ethyl N-(2-(4-benzyloxyphenyl)acetyl)-N-(4-methylthiophenyl)glycinate (VIIq) in 25 mL dry dichloromethane (CH2Cl2) was added 1.05 equivalents of m-chloroperoxybenzoic acid at 0° C. After stirring for 30 min., the solution was poured into 200 mL of saturated NaHCO3 solution containing 10 mL of 10% NaHCO3 solution and was extracted with two 100 mL portions of CH2Cl2. The combined organic extracts were dried over MgSO4 and concentrated to give 1.40 g (ca. 100% yield) of the sulfoxide (VIIt) was an oil.

Workup

  1. extractionwas extracted with two 100 mL portions of CH2Cl2
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d915b4faa1d6421cb0124d7588f89f2d
Source dataset
uspto-grants-1992_04
Patent number
US05109010

Reaction notes

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