m-Chloroperbenzoic acid → HCID 14071489, compound

HRID 2413481Notes

Reaction equation

HRID 2413481 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])=[O:18])=[CH:15][CH:14]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[OH-:45].[Ca+2].[OH-:47]>C(Cl)Cl>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:13]2[CH:27]=[CH:26][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])=[O:18])=[CH:15][CH:14]=2)(=[O:47])=[O:45])=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 6093208Calcium HydroxideHCID 14071487HCID 14071487, compound

Product 1

HCID 14071489HCID 14071489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 1 (400 mg, 0.845 mmoles) was taken up in methylene chloride (30 ml) to which was added m-chloroperbenzoic acid (343 mg, 2 eqts). The reaction mixture was stirred at room temperature under nitrogen for one hour. An additional 20 mg of m-CPBA was added and stirring was continued for one hour. Calcium hydroxide (400 mg) was added to the reaction mixture and stirring was continued for ten minutes. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was triturated with ether to afford the title compound, m.p. 138°-140°.

Workup

  1. stirringstirring
  2. waitwas continued for one hour
  3. stirringstirring
  4. waitwas continued for ten minutes
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-3258ab1bf75040ef9f49e49fd1ec742b
Source dataset
uspto-grants-1988_01
Patent number
US04717736

Reaction notes

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