Methanol → HCID 18358046, compound

HRID 849577Notes

Reaction equation

HRID 849577 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]2[C:22]([O:24]C)=[O:23])=[O:12])[S:2]1.CO.[OH-].[Na+]>O1CCCC1>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]2[C:22]([OH:24])=[O:23])=[O:12])[S:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18358028HCID 18358028, compound

Product 1

HCID 18358046HCID 18358046, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out as described in Example 48, but using 200 mg of methyl 1-[4-(1,2-dithiolan-3-yl)butylcarbamoyl]indoline-2-carboxylate (prepared as described in Example 93), 4 ml of methanol, 2 ml of tetrahydrofuran and 1.0 ml of a 1N aqueous solution of sodium hydroxide. The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue. The mixture was neutralized by the addition of 2N aqueous hydrochloride acid and extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 98 mg of the title compound as a pale yellow amorphous substance having an Rf value of 0.12 (silica gel thin layer chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as developing solvent).

Workup

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  2. additionwas added to the residue
  3. additionThe mixture was neutralized by the addition of 2N aqueous hydrochloride acid
  4. extractionextracted with ethyl acetate
  5. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  8. dissolutionthe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-f15ea93e89944c6b8d6929414a7a6dcd
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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