m-Chloroperbenzoic acid → HCID 91035818, compound

HRID 561882Notes

Reaction equation

HRID 561882 reaction equation
[Cl:1][C:2]1[C:3]([CH2:13][N:14]([CH:47]2[CH2:49][CH2:48]2)[C:15](=[O:46])[CH:16]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][O:36][C:37]3[C:42]([Cl:43])=[CH:41][C:40]([CH3:44])=[CH:39][C:38]=3[Cl:45])=[CH:29][CH:28]=2)[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:55]>ClCCl>[Cl:1][C:2]1[C:3]([CH2:13][N:14]([CH:47]2[CH2:48][CH2:49]2)[C:15](=[O:46])[CH:16]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][O:36][C:37]3[C:42]([Cl:43])=[CH:41][C:40]([CH3:44])=[CH:39][C:38]=3[Cl:45])=[CH:31][CH:32]=2)[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N+:6]([O-:55])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 91185349Tert-butyl (3-[{[5-chloro-2-(methoxypropyl)pyridin-4-yl]methyl}(cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Product 1

HCID 91035818HCID 91035818, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-[{[5-chloro-2-(methoxypropyl)pyridin-4-yl]methyl}(cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Experiment 94, Step 4 in dichloromethane (0.03 M) was added 3-chloroperoxybenzoic acid. The reaction mixture was stirred at RT for 16 h. The reaction was quenched with water and then extracted with EtOAc. The combined organic extracts were washed with 10% aq. HCl and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 1:1 (v/v) Hex:EtOAc 4 EtOAc) afforded the title compound.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with 10% aq. HCl and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 1:1 (v/v) Hex:EtOAc 4 EtOAc)

Sources & evidence

ORD record
ord-7bbd7ad74d934fc1ab4d2d4d5643c0ac
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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