HCID 70054586, compound → HCID 21310958, compound

HRID 583391Notes

Reaction equation

HRID 583391 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH3:31])[C:12]([N:18]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH3:19])=[C:13]([CH:17]=2)[C:14]([OH:16])=[O:15])=[CH:3][CH:2]=1.[H][H]>CO.C(OCC)(=O)C.[Pd]>[C:1]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH3:31])[C:12]([N:18]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH3:19])=[C:13]([CH:17]=2)[C:14]([OH:16])=[O:15])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 70054586HCID 70054586, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21310958HCID 21310958, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.20 g (0.391 mmol) of the product of Example 352 in 25 mL of methanol and 10 mL of ethyl acetate was added 0.050 g of 10% palladium on carbon. The mixture was hydrogenated in a Parr apparatus at 30 psi of hydrogen for 5 h, then filtered through Celite. The Celite pad was washed with 100 mL of methanol and 100 mL of ethyl acetate and the filtrate was concentrated in vacuo. The residue was trituratedwith ether to give 0.173 g (86%) of the carboxylic acid as a pale yellow solid. Electrospray Mass Spec: 514.2 (M-H)-.

Workup

  1. filtrationfiltered through Celite
  2. washThe Celite pad was washed with 100 mL of methanol and 100 mL of ethyl acetate
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-559070506a714650b5d61f21211f7e72
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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