Potassium Hydroxide → HCID 10236477, compound

HRID 858284Notes

Reaction equation

HRID 858284 reaction equation
C([S:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]=1[C:22]([O:24]C)=[O:23])(=O)C.[OH-].[K+]>O1CCOCC1.O>[SH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58763432HCID 58763432, compound

Product 1

HCID 10236477HCID 10236477, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a deoxygenated solution of 3-(2-acetylthioethyl)-1-phenyl-1H-indole-2-carboxylic acid, methyl ester in dioxane (5 mL) was added a deoxygenated solution of potassium hydroxide (0.168 g, 3.0 mmol) in water (5 mL). The reaction mixture was stirred overnight. Volatile solvent was removed under reduced pressure and the remaining mixture was poured into 1 N HCl (25 mL) containing ice chips. The resulting white precipitate was washed with H2O and dried under vacuum to give 0.110 g of 3-(2-mercaptoethyl)-1-phenyl-1H-indole-2-carboxylic acid (93% yield) as a white solid: 1H NMR (CDCl3) δ 1.52 (t, J=8.1 Hz, 1H), 2.91 (q, J=7.7 Hz, 2H), 3.49 (t, J=7.6 Hz, 2H), 7.08 (d, J=8.2 Hz, 1H), 7.21 (t, J=7.5 Hz, 1H), 7.27–7.33 (m, 3H), 7.42–7.53 (m, 3H), 7.78 (d, J=8.0 Hz, 1H). Anal. Calcd. for C17H15N2O2S.0.25 H2O: C, 67.64, H, 5.18, N, 4.64, S, 10.62. Found: C, 67.77, H, 5.15, N, 4.69, S, 10.62.

Workup

  1. customVolatile solvent was removed under reduced pressure
  2. additionthe remaining mixture was poured into 1 N HCl (25 mL)
  3. additioncontaining ice chips
  4. washThe resulting white precipitate was washed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-91bcad5f524c4dc697433d906da8c097
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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