HCID 69420594, compound → HCID 59205302, compound

HRID 2242651Notes

Reaction equation

HRID 2242651 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]([C:22]([N:24]1[CH2:28][CH2:27][C@H:26]([F:29])[CH2:25]1)=[O:23])[C@H:9]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:10]([N:12]([CH3:14])[CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Rh]>[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]([C:22]([N:24]1[CH2:28][CH2:27][C@H:26]([F:29])[CH2:25]1)=[O:23])[C@H:9]([CH:15]1[CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH2:20]1)[C:10]([N:12]([CH3:14])[CH3:13])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 69420594HCID 69420594, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59205302HCID 59205302, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

The material from Step B (0.33 g, 0.77 mmol) was hydrogenated at 50 psi hydrogen in the presence of 5% rhodium on alumina (0.33 g) in methanol (10 mL) using a Parr shaker. After 24 h, the reaction mixture was filtered by passage through a syringe filter. Concentration of the filtrate in vacuo afforded the title compound as a mixture of cis and trans isomers containing a small amount of the fully reduced cyclohexane. LC/MS 430.1 (M+1), 452.1 (M+Na).

Workup

  1. filtrationthe reaction mixture was filtered by passage through a syringe
  2. filtrationfilter

Sources & evidence

ORD record
ord-630c733266914f5bb746edc400a61056
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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