HCID 49833943, compound → HCID 49833949, compound

HRID 1614865Notes

Reaction equation

HRID 1614865 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11]2)=[CH:6][CH:5]=1>CO.[OH-].[Na+]>[O:15]=[C:12]1[CH2:13][CH2:14][C@H:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=2)[CH2:11]1

Participants

4

Reactant 1

HCID 49833943HCID 49833943, compound

Product 1

HCID 49833949HCID 49833949, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(S)-4-(3-Oxo-cyclopentyl)-benzoic acid methyl ester (preparation 19) (10.2 mmol, 2.25 g) was taken up in MeOH (6 mL) and NaOH (2N, 6 mL), the reaction mixture stirred at r.t. for 2 h. Then the MeOH was evaporated and the reaction mixture diluted with water, then neutralized with HCl (2N) to pH 5 and extracted with DCM. Dried over Na2SO4 and concentrated in vacuo to yield the title compound (2.09 g, 99%). 1H NMR (300 MHz, DMSO) δ 12.83 (br s, 1H), 7.94-7.84 (m, 2H), 7.45 (d, 2H), 3.55-3.39 (m, 1H), 2.65-2.52 (m, 1H), 2.41-2.21 (m, 4H), 2.03-1.84 (m, 1H).

Workup

  1. customThen the MeOH was evaporated
  2. additionthe reaction mixture diluted with water
  3. extractionextracted with DCM
  4. dry with materialDried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4899f269dcfd4f3c848bddab5b589af2
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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