Hydrochloric Acid → HCID 67343224, compound

HRID 1669413Notes

Reaction equation

HRID 1669413 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:22][C:21]=2[O:37][CH2:38][O:39][CH3:40])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].Cl>CO>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=2[O:37][CH2:38][O:39][CH3:40])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium Methoxide2×HCID 86627895HCID 86627895, compound

Product 1

HCID 67343224HCID 67343224, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-cyclohexyl-2-(2-(methoxymethoxy)-4-{[(4-methylphenyl)sulfonyl]oxy}-phenyl)-1H-indole-6-carboxylate was suspended in MeOH 0.18 M) and NaOMe (5 eq) was added. The mixture was warmed in a closed vessel to 80° C. After 4 h additional NaOMe (5 eq) was added. The mixture was warmed overnight. The mixture was cooled to RT and 1N aqueous HCl was added to the mixture. After dilution with H2O the mixture was extracted with EtOAc. The organic phase was separated and washed with sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residual material was filtered with PE:EtOAc (8:2) through a pad of silica gel. The product was obtained as a yellowish amorphous solid (49%). (ES+) m/z 410 (M+H)+.

Workup

  1. additionwas added
  2. temperatureThe mixture was warmed overnight
  3. temperatureThe mixture was cooled to RT
  4. extractionAfter dilution with H2O the mixture was extracted with EtOAc
  5. customThe organic phase was separated
  6. washwashed with sat. aq. NaHCO3 and brine
  7. dry with materialAfter drying over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. filtrationThe residual material was filtered with PE

Sources & evidence

ORD record
ord-8b43a9f7d2d64634b101d98226fe029a
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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