HCID 68866398, compound → HCID 68863974, compound

HRID 1725939Notes

Reaction equation

HRID 1725939 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH:16]=[C:15]([CH3:22])[C:14]=2[C:13]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:10])=[O:9]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH:15]([CH3:22])[C:14]=2[C:13]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:10])=[O:9]

Participants

4

Reactant 1

HCID 68866398HCID 68866398, compound

Product 1

HCID 68863974HCID 68863974, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 275E (1.58 g) in 100 mL of ethyl acetate was hydrogenated under 60 psi pressure for 16 hours in the presence of 475 mg of 10% palladium on charcoal. The mixture was filtered, concentrated, treated with diethyl ether, and filtered. The filter cake was washed with diethyl ether to provide 1.5 g of the desired product as a mixture of R and S isomers. MS (ESI(+)) m/e 395 (M+NH4)+; MS (ESI(−)) m/e 376 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.91 (s, 1H), 7.61-7.71 (m, 2H), 7.40-7.46 (m, 1H), 7.31 (dt, 1H), 7.08 (d, 1H), 6.87 (d, 1H), 3.65 (s, 3H), 3.05-3.08 (m, 1H), 2.64-2.78 (m, 2H), 1.58-1.79 (m, 4H), 1.02 (d, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. additiontreated with diethyl ether
  4. filtrationfiltered
  5. washThe filter cake was washed with diethyl ether

Sources & evidence

ORD record
ord-4861589b34334f259dbe412a8a7ea507
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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