m-Chloroperbenzoic acid → HCID 123948265, compound

HRID 2194909Notes

Reaction equation

HRID 2194909 reaction equation
[Cl:1][C:2]1[CH:46]=[C:45]([CH3:47])[CH:44]=[C:43]([Cl:48])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[C:32]([CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[N:33][CH:34]=[CH:35][CH:36]=3)=[CH:27][C:26]=2[CH3:42])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:10][CH:9]=1.ClC1C=C(C=CC=1)C(OO)=[O:54]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:20]([O:19][C:18](=[O:24])[NH:17][CH2:16][CH:15]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[N+:33]([O-:54])[CH:34]=[CH:35][CH:36]=2)=[CH:27][C:26]=1[CH3:42])[CH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][O:4][C:3]2[C:43]([Cl:48])=[CH:44][C:45]([CH3:47])=[CH:46][C:2]=2[Cl:1])=[CH:13][CH:12]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86658855HCID 86658855, compound

Product 1

HCID 123948265HCID 123948265, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl (3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-{4-[2-(3-methoxypropyl)pyridin-3-yl]-2-methylphenyl}propyl)carbamate (1 eq.) from EXAMPLE 16, step 1 in CH2Cl2 (0.03M) at room temperature was added m-chloroperoxybenzoic acid (1.1 eq.). The reaction mixture was stirred for 3 h at room temperature, poured in saturated aqueous NaHCO3 and extracted with EtOAc. The organic extract was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with CH2Cl2/MeOH 5%, afforded the title compound as a foam

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel
  8. washeluting with CH2Cl2/MeOH 5%

Sources & evidence

ORD record
ord-de2dc24cac02442988110052ae234df8
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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