Hydrochloric Acid → HCID 10125929, compound

HRID 858291Notes

Reaction equation

HRID 858291 reaction equation
C[O:2][C:3]([C:5]1[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([O:28]C)=[O:27])[CH:21]=2)[C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][S:16]C(=O)C)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[OH-].[K+].Cl>C1COCC1>[C:26]([C:22]1[CH:21]=[C:20]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]([CH2:14][CH2:15][SH:16])=[C:5]2[C:3]([OH:4])=[O:2])[CH:25]=[CH:24][CH:23]=1)([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58763429HCID 58763429, compound

Product 1

HCID 10125929HCID 10125929, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-acetylsulfanyl-ethyl)-1-(3-methoxycarbonyl-phenyl)-1H-indole-2-carboxylic acid methyl ester (0.32 g, 0.73 mmol) in THF (10 mL) was dropwise added 0.5 N KOH (10 mL) and the resulting mixture was stirred at room temperature overnight. The reaction acidified with 3 N HCl and the resulting white precipitate was washed with H2O and dried under vacuum to give 0.22 g of a white solid (85% yield over 2 steps): 1H NMR (DMSO-d6, 300 MHz) δ 2.81 (t, J=6 Hz, 2H), 3.37 (t, J=6 Hz, 2H), 7.02 (d, J=9 Hz, 1H), 7.19 (t, J=6 Hz, 1H), 7.28 (t, J=6 Hz, 1H), 7.63 (m, 2H), 7.77 (s, 1H), 7.83 (d, J=9 Hz, 1H), 8.01 (d, J=9 Hz, 1H); 13C NMR (DMSO-d6, 300 MHz) δ 25.18, 29.62, 111.11, 121.26, 123.93, 126.18, 127.13, 127.28, 128.35, 129.10, 129.86, 132.24, 138.93, 139.48, 162.78, 167.07. Anal. Calcd for C18H15NO4S: C, 63.33; H, 4.43; N, 4.10; S, 9.39. Found: C, 63.03; H, 4.6; N, 4.09; S, 9.16.

Workup

  1. washthe resulting white precipitate was washed with H2O
  2. customdried under vacuum

Sources & evidence

ORD record
ord-ce94b5fc8fbe4db4a48023a5c205dacd
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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