m-Chloroperbenzoic acid → HCID 86745530, compound

HRID 379639Notes

Reaction equation

HRID 379639 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)/[C:3]=1[CH2:20][CH2:21][N:22]([OH:26])C(N)=O.ClC1C=C(C=CC=1)C(OO)=[O:32]>ClCCl>[NH:22]([CH2:21][CH2:20][C:3]1/[C:4](=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:19])=[O:32])=[CH:16][CH:17]=2)/[C:5]2[C:10]([C:2]=1[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)[OH:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9969171HCID 9969171, compound

Product 1

HCID 86745530HCID 86745530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the hydroxylamine from Example 16, Step 6 (130 mg, 0.40 mmol) in dichloromethane (5 mL) at 0° C. was added in one portion 850% m-chloroperoxy benzoic acid (90 mg, 0.44 mmol, 1.1 eq.). After 45 minutes the reaction mixture was diluted with dichloromethane and washed successively with 1N aqueous sodium hydroxide, water, brine, dried over MgSO4 and evaporated to dryness. The residue was chromatographed on silica gel eluting with a 30:1 mixture of dichloromethane:methanol to yield the title compound as yellow oil.

Workup

  1. washwashed successively with 1N aqueous sodium hydroxide, water, brine
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was chromatographed on silica gel eluting with a 30:1 mixture of dichloromethane

Sources & evidence

ORD record
ord-a359962edd1d44e9b17fe7ff32b53008
Source dataset
uspto-grants-2001_10
Patent number
US06300346B1

Reaction notes

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