HCID 58868869, compound → HCID 58868834, compound

HRID 1441962Notes

Reaction equation

HRID 1441962 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6](/[CH:8]=[C:9](\[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:7]=1.[H][H]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:5]([F:28])=[CH:4][CH:3]=1)[CH2:8][C@@H:9]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22]

Participants

4

Reactant 2

HCID 58868869HCID 58868869, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58868834HCID 58868834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.0 g (13.3 mmol) of benzyl (2Z)-3-(5-bromo-2-fluorophenyl)-2-[(tert-butoxycarbonyl)amino]acrylate are dissolved in 100 ml of ethanol. Under an argon atmosphere, 40 mg (0.055 mmol) of (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)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 bar of hydrogen for 4 days. The mixture is filtered through silica gel, which is carefully washed with ethanol. The filtrate is concentrated in vacuo, and the crude product is dried under high vacuum.

Workup

  1. filtrationThe mixture is filtered through silica gel, which
  2. washis carefully washed with ethanol
  3. concentrationThe filtrate is concentrated in vacuo
  4. dry with materialthe crude product is dried under high vacuum

Sources & evidence

ORD record
ord-3ad29dde2be74e5797d82d1d09b47e55
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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