Acetic Acid → 5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid

HRID 2057335Notes

Reaction equation

HRID 2057335 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([CH3:15])[CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br-].[C:18]([CH2:21][CH2:22][CH2:23][CH2:24][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:20])=[O:19].[H-].[Na+].CC(O)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:7]([CH3:15])[CH:8]1[CH2:13][CH2:12][C:11](=[CH:24][CH2:23][CH2:22][CH2:21][C:18]([OH:20])=[O:19])[CH2:10][CH2:9]1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 24820328tert-butyl N-methyl-N-(4-oxocyclohexyl)carbamate

Product 1

HCID 225676825-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5 g (21.99 mmol) Methyl-(4-oxo-cyclohexyl)-carbamic acid tert-butyl ester and 12.68 g (28.59 mmol) (4-Carboxy-butyl)-triphenyl-phosphonium bromide were dispended in 50 ml DMF. In small portions 2.49 g (57.2 mmol, 55%) NaH were added and the slurry was diluted by adding 50 ml DMF. The mixture was stirred at RT over night, 10 ml AcOH were added and the solvent was evaporated under reduced pressure. The residue was dissolved in ether and water, and the inorganic layer was extracted with ether. The combined organic phases were dried over and the crude materil was purified by column chromatography with ETOAc/hexane to give 5.86 g (83%) 5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid.

Workup

  1. additionthe slurry was diluted
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. extractionwater, and the inorganic layer was extracted with ether
  5. customThe combined organic phases were dried over and the crude materil
  6. customwas purified by column chromatography with ETOAc/hexane

Sources & evidence

ORD record
ord-805d74d3a676472f874addc9352112b7
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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