m-Chloroperbenzoic acid → HCID 86635949, compound

HRID 561892Notes

Reaction equation

HRID 561892 reaction equation
[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[CH:42][N:41]=[CH:40][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:49]>ClCCl>[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[CH:42][N+:41]([O-:49])=[CH:40][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])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86635948tert-Butyl (3-[cyclopropyl(pyridin-4-ylmethyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Product 1

HCID 86635949HCID 86635949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-[cyclopropyl(pyridin-4-ylmethyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 110, Step 1 (1 eq.) in dichloromethane (0.12 M) was added 3-chloroperoxybenzoic acid (1.3 eq.). The reaction mixture was stirred at RT for 1.5 h. The reaction was then quenched with 10% aq. Na2S2O3 and sat. aq. NaHCO3. The organic layer was separated and the aqueous layer were back extracted with ether. The combined organic extracts were washed with water, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, EtOAc→4:1 (v/v) EtOAc:MeOH) afforded the title compound.

Workup

  1. customThe reaction was then quenched with 10% aq. Na2S2O3 and sat. aq. NaHCO3
  2. customThe organic layer was separated
  3. extractionthe aqueous layer were back extracted with ether
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, EtOAc→4:1 (v/v) EtOAc:MeOH)

Sources & evidence

ORD record
ord-bd1bd632c0b54c2395291418d5927c54
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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