HCID 67185843, compound → HCID 67188462, compound

HRID 1441963Notes

Reaction equation

HRID 1441963 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6](/[CH:8]=[C:9](\[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])/[C:10]([O:12][CH3:13])=[O:11])[CH:7]=1.[H][H]>C(O)C.O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:5]([F:22])=[CH:4][CH:3]=1)[CH2:8][C@@H:9]([C:10]([O:12][CH3:13])=[O:11])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 67185843HCID 67185843, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67188462HCID 67188462, compound

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Procedure

20 g (53.45 mmol) of methyl (2Z)-3-(5-bromo-2-fluorophenyl)-2-[(tert-butoxycarbonyl)amino]acrylate (Example 4O) are dissolved in 300 ml of ethanol/dioxane (3:1). Under an argon atmosphere, 200 mg of (+)-1,2-bis((2S,5S)-2,5-diethylphospolano)benzene(cyclooctadiene)rhodium(I)trifluoromethanesulfonate are added, and argon is passed through the solution for 30 min. The mixture is then hydrogenated under a pressure of 3.5 bar of hydrogen for 3 days. The solvent is removed on a rotary evaporator, and the crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 2:2).

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. customthe crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 2:2)

Sources & evidence

ORD record
ord-8650d4eab49a4a148d7b1f6abd85c48a
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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