m-Chloroperbenzoic acid → HCID 70317890, compound

HRID 2181271Notes

Reaction equation

HRID 2181271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([S:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:14][CH2:13][CH:12]([NH:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17])[CH2:11][CH2:10]1.ClC1C=C(C=CC=1)C(OO)=[O:40]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([S:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH2:14][CH2:13][CH:12]([NH:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:40])=[O:17])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70320026HCID 70320026, compound

Product 1

HCID 70317890HCID 70317890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from Example 65 (110 mg, 0.21 mmol) in dichloromethane (2 ml) was treated with m-chloroperoxybenzoic acid (86 mg, 0.25 mmol, 50% w/w) and stirred for 1 hour. The reaction was diluted with dichloromethane (25 ml) and washed with sodium bisulfite (30 ml, 10% solution), saturated sodium bicarbonate (30 ml) and brine (20 ml), dried over magnesium sulfate, evaporated and purified by silica gel chromatography eluting the desired product with ethyl acetate/hexane mixtures, 80 mg. 1H NMR δ(ppm) (CDCl3), 7.66 (2H, d, J=7.5 Hz), 7.53 (2H, d, J=7.5 Hz), 7.08-7.04 (2H, m), 6.90-6.78 (1H, m), 4.32 (1H, d, J=7.9 Hz), 3.64-3.55 (1H, m), 2.62-2.53 (2H, m), 2.48-2.38 (2H, m), 2.21-1.98 (2H, m), 1.65-1.54 (2H, m), 1.40 (9H, s), MS MH=540.

Workup

  1. washwashed with sodium bisulfite (30 ml, 10% solution), saturated sodium bicarbonate (30 ml) and brine (20 ml)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. custompurified by silica gel chromatography
  5. washeluting the desired product with ethyl acetate/hexane mixtures, 80 mg

Sources & evidence

ORD record
ord-a707c0b283ab42ad8326b883e2a91f1c
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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