Hydrochloric Acid → HCID 10850547, compound

HRID 1866805Notes

Reaction equation

HRID 1866805 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:23])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.C1COCC1.O.Cl>C(OCC)(=O)C.O>[NH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([S:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][C:5]([OH:23])=[O:4])=[CH:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10827865HCID 10827865, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 10850547HCID 10850547, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

LiOH (1.6 g, 67.3 mmol) is added to [2-(1H-indol-3-ylsulfanyl)-phenyl]-acetic acid methyl ester (2 g, 6.73 mmol) in 27 mL mixture of THF/water (20:7). The reaction mixture is stirred for 10 minutes at 150° C. in a Emrys Optimizer EXP microwave reactor under microwave heating and cooled to room temperature. The reaction mixture is poured into water and acidified with concentrated HCl. Ethyl acetate is added and the organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give the title compound, which is used in the next step without further purification.

Workup

  1. temperatureheating
  2. temperaturecooled to room temperature
  3. washthe organic phase is washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f45f9b565e874825ab7cb639d189e041
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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