HCID 67298297, compound → HCID 67298331, compound

HRID 1620934Notes

Reaction equation

HRID 1620934 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[CH:5][CH2:6][C:7]([F:10])([F:9])[F:8]>C(O)C>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8]

Participants

3

Reactant 1

HCID 67298297HCID 67298297, compound

Product 1

HCID 67298331HCID 67298331, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Benzyloxycarbonylamino-5,5,5-trifluoropent-2-enoic acid methylester (15.37 g, 48.5 mmol) was dissolved in absolute ethanol (100 mL) in a Parr hydrogenation vessel. The solution was sparged with a stream of nitrogen and then (+)Duphos (350 mg) was added. The reaction mixture was placed on a Parr hydrogenation apparatus and the headspace was evacuated and then pressurized with 50 psi of hydrogen. This process was repeated seven times and the vessel was then pressurized with 50 psi of hydrogen and agitated on the Parr apparatus overnight. The reaction mixture was then concentrated by rotary evaporation, dissolved in 1:1 ethyl acetate:hexanes, and filtered through a bed of silica to remove catalyst. The filtrate was concentrated by rotary evaporation yielding crude (S)-2-benzyloxycarbonylamino-5,5,5-trifluoropentanoic acid methyl ester that was carried forward without further purification.

Workup

  1. customThe solution was sparged with a stream of nitrogen
  2. addition(+)Duphos (350 mg) was added
  3. customthe headspace was evacuated
  4. concentrationThe reaction mixture was then concentrated by rotary evaporation
  5. dissolutiondissolved in 1:1 ethyl acetate
  6. filtrationhexanes, and filtered through a bed of silica
  7. customto remove catalyst
  8. concentrationThe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-7b969f012da24333a9325aa95dfd6591
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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