m-Chloroperbenzoic acid → HCID 86635946, compound

HRID 561886Notes

Reaction equation

HRID 561886 reaction equation
[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH2:46][CH2:47][S:48]([CH3:51])(=[O:50])=[O:49])[N:41]=[C:40]([CH2:52][CH2:53][CH2:54][O:55][CH3:56])[CH:39]=2)[C:5](=[O:36])[CH:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][O:26][C:27]3[C:32]([Cl:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[Cl:35])=[CH:19][CH:18]=2)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:62]>ClCCl>[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH2:46][CH2:47][S:48]([CH3:51])(=[O:49])=[O:50])[N+:41]([O-:62])=[C:40]([CH2:52][CH2:53][CH2:54][O:55][CH3:56])[CH:39]=2)[C:5](=[O:36])[CH:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][O:26][C:27]3[C:32]([Cl:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[Cl:35])=[CH:19][CH:18]=2)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86635944HCID 86635944, compound

Product 1

HCID 86635946HCID 86635946, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (0.06 M) of tert-butyl (3-[cyclopropyl({2-(3-methoxypropyl)-6-[3-(methylsulfonyl)propoxy]pyridin-4-yl]methyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 101, Step 1 (1 eq.) was added 3-chloroperoxybenzoic acid (3.6 eq.). The resulting solution was stirred at RT for 18 h. The reaction was quenched with sat. aq. NaHCO3 and then extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 90:10 (v/v) CH2Cl2:EtOH→85:15 (v/v) CH2Cl2:EtOH) afforded the title compound.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 90:10 (v/v) CH2Cl2:EtOH→85:15 (v/v) CH2Cl2:EtOH)

Sources & evidence

ORD record
ord-6373d13b199d4bb28fe1d72c02040588
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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