Hydrochloric Acid → HCID 59332672, compound

HRID 387281Notes

Reaction equation

HRID 387281 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])[C:25]([CH3:32])([CH3:31])[CH2:24]1.[OH-].[Na+].Cl>CO.O>[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])[C:25]([CH3:32])([CH3:31])[CH2:24]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59332590HCID 59332590, compound

Product 1

HCID 59332672HCID 59332672, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

1-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (685 mg, 1.296 mmol) was placed in a flask and dissolved in methanol (6 mL) and water (3 mL). An aqueous solution of sodium hydroxide 6N in water (3.24 mL, 19.44 mmol) was added. The mixture was heated in a microwave for 30 mins at 80° C. The mixture was acidified with aqueous HCl 1N until pH=1, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and the solvent removed under vacuum to afford 490 mg of the title compound as a yellow powder.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ca11e832d9ab4c059438081c25643dcd
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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