Hydrochloric Acid → HCID 18427727, compound

HRID 650413Notes

Reaction equation

HRID 650413 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=3)[CH:20]([C:31]3[CH:36]=[CH:35][C:34]4[O:37][CH2:38][O:39][C:33]=4[CH:32]=3)[CH:19]2[C:40]([O:42]C)=[O:41])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[OH-].[Na+].Cl>CC(O)C.O>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=3)[CH:20]([C:31]3[CH:36]=[CH:35][C:34]4[O:37][CH2:38][O:39][C:33]=4[CH:32]=3)[CH:19]2[C:40]([OH:42])=[O:41])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86757246HCID 86757246, compound

Product 1

HCID 18427727HCID 18427727, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Methyl (1RS,2SR,3RS)-3-[2-(3Carboxyphenyl)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (0.08 g, crude) was dissolved in propan-2-ol (I ml) and aqueous sodium hydroxide (1M, 1 ml ,l mmol) added. The mixture was refluxed for 12 hr. then cooled, diluted with water, acidified with 3M-aqueous hydrochloric acid and extracted with ethyl acetate (3×). The combined organic extract was purified by column chromatography on silical-gel (eluant: 30% EtOAc/hexane/5% AcOH) to give the title compound as a colorless solid (20 mg)

Workup

  1. temperatureThe mixture was refluxed for 12 hr
  2. temperaturethen cooled
  3. extractionextracted with ethyl acetate (3×)
  4. extractionThe combined organic extract
  5. customwas purified by column chromatography on silical-gel (eluant: 30% EtOAc/hexane/5% AcOH)

Sources & evidence

ORD record
ord-e309a8f9e2df4050b3ff6361f7aefb6b
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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