Potassium Hydroxide → HCID 9899539, compound

HRID 1583119Notes

Reaction equation

HRID 1583119 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[C:9]([CH2:10][C:11]([O:13]C)=[O:12])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:15][CH2:16][S:17]C(=O)C.[OH-].[K+]>CCO>[C:11]([CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:15][CH2:16][SH:17])[C:4]=1[C:3]([OH:21])=[O:2])([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20728722HCID 20728722, compound

Product 1

HCID 9899539HCID 9899539, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A deoxygenated mixture of 2-(2-acetylsulfanyl-ethyl)-6-methoxycarbonylmethyl-benzoic acid methyl ester (0.555 g, 1.77 mmol) and 6 N KOH (3 mL) in EtOH (7 mL) was heated at reflux for 18 h. After allowing to cool to rt, the mixture was partitioned between 1 N HCl (75 mL) and EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over MgSO4 and concentrated in vacuo. The crude product was dissolved in ether (100 mL), filtered to remove some unidentified solid material, and concentrated to give 2-carboxymethyl-6-(2-mercapto-ethyl)-benzoic acid as a white solid (0.310 g, 73%): 1H NMR (CDCl3) δ1.37 (t, J=8.2 Hz, 1H), 2.76 (m, 2H), 3.06 (m, 2H), 3.90 (s, 2H), 7.10 (d, J=7.6 Hz, 1H), 7.21 (d, J=6.9 Hz, 1H), 7.34 (t, J=7.8 Hz, 1H): 13C NMR (CDCl3) δ27.25, 40.43, 41.83, 131.58, 131.64, 132.45, 132.55, 134.66, 141.41, 176.14, 179.40. Anal. Calcd for C, H11H12O4S: C, 54.99; H, 5.03; S, 13.35. Found: C, 55.20; H, 5.26; S, 13.32.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customthe mixture was partitioned between 1 N HCl (75 mL) and EtOAc (100 mL)
  4. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude product was dissolved in ether (100 mL)
  8. filtrationfiltered
  9. customto remove some unidentified solid material
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9f6a0545a60f49899fe968a2bfa30c93
Source dataset
uspto-grants-2004_05
Patent number
US06740777B2

Reaction notes

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