HCID 67170252, compound → HCID 67169865, compound

HRID 1918302Notes

Reaction equation

HRID 1918302 reaction equation
C([O:8][CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1([NH:17][C:18](=[O:37])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=2)[CH:20]=1)[C:14]([OH:16])=[O:15])C1C=CC=CC=1>C(O)C.[Pd].[H][H]>[OH:8][CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1([NH:17][C:18](=[O:37])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=2)[CH:20]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 1

HCID 67170252HCID 67170252, compound

Product 1

HCID 67169865HCID 67169865, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 23938PalladiumSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Diastereomer 1 and diastereomer 2 of the compound of example 66 were separately dissolved in ethanol and hydrogenated with palladium 10% on charcoal at room temperature with 1 bar hydrogen pressure until completion of the reaction. After filtration, the solutions were evaporated to dryness and the residues purified by RP HPLC (water/ACN gradient) to yield the two diastereomers of the title compound separately.

Workup

  1. filtrationAfter filtration
  2. customthe solutions were evaporated to dryness
  3. customthe residues purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-4225b81eaec4410ba8f5ac8d71251e15
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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