HCID 67021720, compound → HCID 67021693, compound

HRID 40791Notes

Reaction equation

HRID 40791 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C@H:13]([N:15]([CH2:25][O:26][CH3:27])[S:16]([CH2:19][CH2:20]/[CH:21]=[CH:22]/[CH2:23][OH:24])(=[O:18])=[O:17])[CH3:14])[CH:9]=[CH:10][C:11]=2[F:12])[CH2:3][CH2:2]1>C(OCC)(=O)C.[C].[Pd]>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C@H:13]([N:15]([CH2:25][O:26][CH3:27])[S:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])(=[O:18])=[O:17])[CH3:14])[CH:9]=[CH:10][C:11]=2[F:12])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67021720HCID 67021720, compound

Product 1

HCID 67021693HCID 67021693, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The (R,E)-N-(1-(3-(cyclopropylmethoxy)-4-fluorophenyl)ethyl)-5-hydroxy-N-(methoxymethyl)pent-3-ene-1-sulfonamide (296 mg) obtained in Reference Example 186 was dissolved in ethyl acetate (5.0 mL). To the solution, 10% palladium-carbon (170 mg) was added, and the reaction mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere. The precipitate was removed by filtration through a pad of Celite and washed with ethyl acetate (100 mL). Then, the combined filtrate was concentrated under reduced pressure to obtain the title compound (208 mg) as a crude product.

Workup

  1. customThe precipitate was removed by filtration through a pad of Celite
  2. washwashed with ethyl acetate (100 mL)
  3. concentrationThen, the combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aecc7adb11fb44c7a069da969b0247b3
Source dataset
uspto-grants-2013_09
Patent number
US08530490B2

Reaction notes

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