m-Chloroperbenzoic acid → tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-oxiran-2-ylphenyl)ethyl]carbamate

HRID 511012Notes

Reaction equation

HRID 511012 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[C:12]([CH:18]=[CH2:19])[C:11]=1[O:20][CH3:21])[CH3:9])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[C:12]([CH:18]2[CH2:19][O:31]2)[C:11]=1[O:20][CH3:21])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 123890412tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethyl]carbamate

Product 1

HCID 123871195tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-oxiran-2-ylphenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethyl]carbamate (460 mg, 1.4 mmol, from Example 189, Step 1) was stirred in methylene chloride (4.6 mL) and m-chloroperbenzoic acid (2.1 g, 8.5 mmol) was added. The mixture was stirred overnight at room temperature. The suspension was filtered and the collected solids were washed with methylene chloride. The filtrates were evaporated to give the desired compound.

Workup

  1. filtrationThe suspension was filtered
  2. washthe collected solids were washed with methylene chloride
  3. customThe filtrates were evaporated

Sources & evidence

ORD record
ord-9fce1da57c8641e9a86e02d411091df0
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

Loading…