Methyl Acrylate → Methyl(2E)-5-{(tert-butylsulfinyl)[4-(trifluoromethyl)benzyl]amino}-5-[4-(trifluoromethyl)phenyl]pent-2-enoate

HRID 1869764Notes

Reaction equation

HRID 1869764 reaction equation
[CH3:1][C:2]([S:5]([N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[CH2:9][CH:10]=[CH2:11])=[O:6])([CH3:4])[CH3:3].[C:33]([O:37][CH3:38])(=[O:36])C=C>>[C:2]([S:5]([N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][CH:24]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[CH2:9]/[CH:10]=[CH:11]/[C:33]([O:37][CH3:38])=[O:36])=[O:6])([CH3:1])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 7294Methyl AcrylateHCID 579874802-Methyl-N-[4-(trifluoromethyl)benzyl]-N-{1-[4-(trifluoromethyl)phenyl]but-3-en-1-yl}propane-2-sulfinamide

Product 1

HCID 57987395Methyl(2E)-5-{(tert-butylsulfinyl)[4-(trifluoromethyl)benzyl]amino}-5-[4-(trifluoromethyl)phenyl]pent-2-enoate

Procedure

The alkene from Step 2 (800 mg, 1.67 mmol) was dissolved in methyl acrylate (1.5 mL) and Zhan I catalyst (110 mg) was added. This mixture was stirred for 30 min and TLC indicated all starting material had reacted. The mixture was evaporated and purified by chromatography on silica using 10-25% ethyl acetate in iso-hexane to give the product (500 mg) as a mixture of isomers:

Workup

  1. customhad reacted
  2. customThe mixture was evaporated
  3. custompurified by chromatography on silica using 10-25% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-50871c1254d54f7b9aa12ddd7aee3668
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

Loading…