Water → HCID 178471547, compound

HRID 1403128Notes

Reaction equation

HRID 1403128 reaction equation
[H-].[Na+].[CH:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:6]1)=O.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20].O>O1CCCC1>[C:14]([O:13][C:12]([NH:11][C@H:8]1[CH2:9][CH2:10][C@H:5](/[CH:3]=[CH:20]/[C:19]([O:22][CH2:23][CH3:24])=[O:21])[CH2:6][CH2:7]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178453955HCID 178453955, compound

Product 1

HCID 178471547HCID 178471547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethyl phosphonoacetate (107 mg) was dissolved in tetrahydrofuran (1 mL), and 60% sodium hydride (19 mg) was added thereto, followed by stirring at room temperature for 30 minutes. A solution of tert-butyl (trans-4-formylcyclohexyl)carbamate (90 mg) in tetrahydrofuran (1 mL) was added dropwise thereto, followed by stirring at room temperature for 2 hours. Ethyl acetate and water were added thereto, followed by extraction with ethyl acetate. The extracts were washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-50:50) to obtain ethyl (2E)-3-{trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl}acrylate (100 mg).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extracts were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-50:50)

Sources & evidence

ORD record
ord-2371c5903c184c7f8dcf7d6c92b27c60
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…