HCID 54170481, compound → 4-((R)-1-methylheptyloxycarbonyl)benzoic acid

HRID 1426Notes

Reaction equation

HRID 1426 reaction equation
C([O:8][C:9](=[O:27])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][C@H:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:17])=[CH:12][CH:11]=1)C1C=CC=CC=1.[H][H]>[Pd].O1CCCC1>[CH3:26][C@@H:19]([O:18][C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:9]([OH:27])=[O:8])=[CH:15][CH:14]=1)=[O:17])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 54170481HCID 54170481, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 539262054-((R)-1-methylheptyloxycarbonyl)benzoic acidYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Then, 0.12 g of 5% palladium/carbon and 30 ml of a tetrahydrofuran solution containing 1.21 g of 4-((R)-1-methylheptyloxycarbonyl)benzoic acid benzyl ester were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed using Celite as a filter aid, and the filtrate was concentrated. The concentrate obtained was purified by column chromatography to obtain 0.91 g of 4-((R)-1-methylheptyloxycarbonyl)benzoic acid as a colorless liquid (gradually crystallized) (isolated yield: 99%).

Workup

  1. custom5% palladium/carbon was removed
  2. concentrationthe filtrate was concentrated
  3. customThe concentrate obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-788333422f5e4a87925a5f9214f163ee
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Reaction notes

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