Trifluoroacetic acid → HCID 58626993, compound

HRID 983689Notes

Reaction equation

HRID 983689 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C@@:8]1([CH2:14][C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][C@@H:10]([CH3:13])[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:5][C:6]([CH2:7][C@:8]1([CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:11][C@@H:10]([CH3:13])[CH2:9]1)=[O:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58626990HCID 58626990, compound

Product 1

HCID 58626993HCID 58626993, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(1S,3R)-1-Methoxycarbonylmethyl-3-methyl-cyclopentyl]-acetic acid tert-butyl ester (6.64 g, 24.6 mmol) and trifluoroacetic acid (10 mL) were stirred together in dichloromethane (30 mL) for 17 hours at room temperature. The mixture was carefully poured into aqueous sodium carbonate and extracted with ethyl acetate (200 mL). The aqueous was acidified to pH 1 with concentrated hydrochloric acid and re-extracted with ethyl acetate (3×200 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by chromatography (silica gel, eluting with a gradient of heptane to 1:1 heptane:ethyl acetate) to give 5.26 g (100%) of [(1R,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl]-acetic acid;

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. extractionre-extracted with ethyl acetate (3×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel
  6. washeluting with a gradient of heptane to 1:1 heptane

Sources & evidence

ORD record
ord-8b449ac9785e419e8978091e612ef64a
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

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