Hydrochloric Acid → HCID 67346125, compound

HRID 1669492Notes

Reaction equation

HRID 1669492 reaction equation
Cl.[CH:2]1([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29]COC)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>CO>[CH:2]1([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[OH:29])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67346622HCID 67346622, compound

Product 1

HCID 67346125HCID 67346125, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

3 M HCl (aq) (4 eq) was added to a stirred mixture of methyl 3-cyclohexyl-2-[4-methoxy-2-(methoxymethoxy)phenyl]-1H-indole-6-carboxylate in MeOH (0.05 M) and the mixture was stirred at 80° C. for 2 h. The mixture was cooled, solvents were concentrated in vacuo and the residue diluted with EtOAc, washed with sat. aq. NaHCO3, brine, dried (Na2SO4), filtered and the solvent was removed in vacuo to afford the title compound (95%). (ES+) m/z 380 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationsolvents were concentrated in vacuo
  3. additionthe residue diluted with EtOAc
  4. washwashed with sat. aq. NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-058e5db309a748fa8fbe786c695af750
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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