HCID 58022609, compound → HCID 58022560, compound

HRID 445430Notes

Reaction equation

HRID 445430 reaction equation
[CH2:1]([C@@:4]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[CH:15][C:14]=1[Cl:30])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[C:35]([O:34][C:32]([NH:31][C@:4]([CH2:1][CH2:2][CH3:3])([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)=[CH:15][C:14]=1[Cl:30])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 1

HCID 58022609HCID 58022609, compound

Product 1

HCID 58022560HCID 58022560, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Example 13 (400 mg) in ethyl acetate (20 mL) was added palladium, on activated carbon/ethylene diamine complex (100 mg), and the resultant solution was stirred at room temperature for 24 hours under hydrogen atmosphere. The reaction solution was filtered through Celite, and the solvent was evaporated. The resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain the target product (293 mg) as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customthe solvent was evaporated
  3. customThe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-11a133618dcb45ceb30a780bea2a0885
Source dataset
uspto-grants-2013_07
Patent number
US08476305B2

Reaction notes

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