Hydrochloric Acid → HCID 59332684, compound

HRID 656047Notes

Reaction equation

HRID 656047 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]CC)=[O:12])[CH:10]=1)[N:7](C(OC(C)(C)C)=O)[CH:6]=[C:5]2[CH:23]1[CH2:28][CH2:27][S:26](=[O:30])(=[O:29])[CH:25]([CH:31]([CH3:33])[CH3:32])[CH2:24]1.O.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:23]1[CH2:28][CH2:27][S:26](=[O:29])(=[O:30])[CH:25]([CH:31]([CH3:33])[CH3:32])[CH2:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59332712HCID 59332712, compound

Product 1

HCID 59332684HCID 59332684, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-[2-(1-methylethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]-1H-indole-1,7-dicarboxylate (1.46 g, 2.69 mmol) was dissolved in methanol (12 mL) and then water (6.00 mL) was added and then 6 N aqueous NaOH (6.73 mL, 40.4 mmol was added and the mixture was heated in a microwave 30 mins at 80° C. The mixture was neutralized with 1 N aqueous HCl until pH=1 and a small amount of yellow solid precipitated which was set aside. The aqueous solution was extracted with ethyl acetate, the organic layers were combined, dried (MgSO4) and solvent was removed under vacuum to afford the title compound.

Workup

  1. customa small amount of yellow solid precipitated which
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialdried (MgSO4) and solvent
  4. customwas removed under vacuum

Sources & evidence

ORD record
ord-00e9d340afbd401e9ccbc68c33ff2796
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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