HCID 131735598, compound → HCID 121324403, compound

HRID 527329Notes

Reaction equation

HRID 527329 reaction equation
[C:1]([S@:5]([NH:7][C@@:8]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])([CH:19]([F:21])[F:20])[C:9]([F:18])([F:17])[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([S@:5]([NH:7][C@@:8]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])([CH:19]([F:21])[F:20])[C:9]([F:17])([F:18])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 131735598HCID 131735598, compound

Product 1

HCID 121324403HCID 121324403, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl (S)-5-(((R)-tert-butylsulfinyl)amino)-4,4,6,6-tetrafluoro-5-(2-fluorophenyl)hex-2-enoate (1.77 g, 4.28 mmol) in ethyl acetate (100 mL) was added Pd/C (400 mg, 10%). The black suspension was stirred at 25° C. for 18 hours under 45-50 psi H2. It was filtrated and concentrated to give ethyl (S)-5-(((R)-tert-butylsulfinyl)amino)-4,4,6,6-tetrafluoro-5-(2-fluorophenyl)hexanoate (1.70 g, 95.5% yield) which was used in the next step immediately without further purification.

Workup

  1. filtrationIt was filtrated
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-acab955f278f4c0bb63ea5cc5915e074
Source dataset
uspto-grants-2016_05
Patent number
US09346797B1

Reaction notes

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