m-Chloroperbenzoic acid → HCID 15605226, compound

HRID 1364504Notes

Reaction equation

HRID 1364504 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:27]3[CH:26]=[C:25]([CH3:28])[C@:24]([CH2:30][CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)[OH:32])([CH3:29])[CH2:23][C:22]=3[CH:21]=[N:20]2)=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[C:27]3[CH:26]=[C:25]([CH3:28])[C@:24]([CH2:30][CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N+:34]=4[O-:6])[OH:32])([CH3:29])[CH2:23][C:22]=3[CH:21]=[N:20]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15605172HCID 15605172, compound

Product 1

HCID 15605226HCID 15605226, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-chloroperoxybenzoic acid (28 mg, 1.5 eq) was added to a solution of the diastereomer mixture of the alcohols from Examples 75 and 76 in chloroform (3 mL) at room temperature. After 3 h, the mixture was quenched with saturated NaHCO3 (1 mL), diluted with EtOAc (60 mL), washed with water (5 mL), brine (5 mL), dried (MgSO4) and concentrated. Reverse phase HPLC purification (MeOH-water, 50 to 100%) yielded the desired N-oxide as a mixture of two diastereomers (5 mg), which was separated by chiral OD column (isocratic, i-PrOH/heptane, 15%) to give Examples 78 (1.3 mg, 3%, isomer A, faster eluent) and 79 (1.5 mg, 4%, isomer B, slower eluent). MS found: (M+H)+=380.

Workup

  1. customthe mixture was quenched with saturated NaHCO3 (1 mL)
  2. additiondiluted with EtOAc (60 mL)
  3. washwashed with water (5 mL), brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customReverse phase HPLC purification (MeOH-water, 50 to 100%)

Sources & evidence

ORD record
ord-dec7a9ad4e3c421580f66224bf2da1c6
Source dataset
uspto-grants-2011_02
Patent number
US07888381B2

Reaction notes

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