HCID 131736933, compound → HCID 131736932, compound

HRID 56430Notes

Reaction equation

HRID 56430 reaction equation
C(OC([NH:11][CH:12]1[CH:17]([NH:18][C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:16][CH2:15][CH:14]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:13]1)=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)(C)C>[NH2:11][CH:12]1[CH:17]([NH:18][C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:25])[CH3:26])=[O:20])[CH2:16][CH2:15][CH:14]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:13]1

Participants

5

Reactant 2

HCID 131736933HCID 131736933, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131736932HCID 131736932, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of Racemate-ethyl 3-(benzyloxycarbonylamino)-4-((2-(trimethylsilyl)ethoxy)carbonylamino)cyclohexanecarboxylate (1.7 g, 3.7 mmol) and 5% palladium on carbon (50% wet, 300 mg) in isopropanol (35 mL) was stirred under 1 atm hydrogen atmosphere at room temperature for 18 hours. The mixture was filtered through a pad of celite. The filtrate was concentrated and purified by silica gel chromatography (methanol/dichloromethane=1/30 to 1/10) to afford the title compound (1.0 g, 89%) as a yellow oil. MS (ES+) C15H30H2O4Si requires: 330, found: 331 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel chromatography (methanol/dichloromethane=1/30 to 1/10)

Sources & evidence

ORD record
ord-781e6d020dec40c883ca71bea9c731b9
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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