m-Chloroperbenzoic acid → HCID 19884813, compound

HRID 846225Notes

Reaction equation

HRID 846225 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15][CH:14]=2)=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[OH-:46].[Ca+2].[OH-:48]>C(Cl)Cl>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15][CH:14]=2)(=[O:48])=[O:46])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 6093208Calcium HydroxideHCID 67916683HCID 67916683, compound

Product 1

HCID 19884813HCID 19884813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound of Step B above, (1.0 g, 2.05 mmoles) was dissolved in dry methylene chloride (25 ml) to which was added one equivalent of m-chloroperbenzoic acid in methylene chloride (10 ml). After 1 hour stirring at room temperature, additional m-CPBA (450 mg) was added. The reaction was complete in two hours Calcium hydroxide (1.0 g) was added and the reaction mixture was stirred for 10 minutes. The mixture was filtered and the filtrate concentrated. The residue was purified by chromatography to yield the title compound. NMR (CDCl3): 0.90 (3H, m), 1.50 (2H, m), 1.74 (4H, m), 2.33 (6H, m), 2.55 (3H, s), 3.03 (2H, m), 3.37 (2H, m), 3.68 (3H, s), 4.12 (2H, m), 6.39 (2H, d), 7.60 (2H, d), 8.12 (4H, m), 12.73 (1H, s).

Workup

  1. waitThe reaction was complete in two hours
  2. stirringthe reaction mixture was stirred for 10 minutes
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-fb6b90461dd646aab204400f7b1bd3f6
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

Loading…