Hydrochloric Acid → HCID 59718797, compound

HRID 383532Notes

Reaction equation

HRID 383532 reaction equation
[OH-].[Na+].CO.[CH:5]1([CH2:11][N:12]2[C:17](=[O:18])[C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][C:14]3[CH2:24][S:25][CH2:26][CH2:27][C:13]2=3)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Cl>O>[CH:5]1([CH2:11][N:12]2[C:17](=[O:18])[C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]3[CH2:24][S:25][CH2:26][CH2:27][C:13]2=3)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59718849HCID 59718849, compound

Product 1

HCID 59718797HCID 59718797, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4M sodium hydroxide solution (15.2 mL, 60.8 mM) was added to a methanol (30 mL) solution of ethyl 1-cyclohexylmethyl-2-oxo-1,5,7,8,tetrahydro-2H-thiopyrano[4,3-b]pyridine-3-carboxylate (AA08, 8.16 g, 24.3 mmol), which had been obtained in Example 8, at room temperature, and the mixture was heated and refluxed for 30 minutes. The reaction mixture was diluted with water (100 mL) and washed with ether (100 mL). 5M hydrochloric acid (13 mL, 65 mmol) was added to the water layer, the precipitated crystal was separated by filtration and washed with water, and the brown crystal of 1-cyclohexylmethyl-2-oxo-1,5,7,8,tetrahydro-2H-thiopyrano[4,3-b]pyridine-3-carboxylic acid (6.78 g) was obtained. The crystal was recrystallized from ethanol-water to give light brown crystalline powder (AA09, 6.30 g, 84.3%).

Workup

  1. customhad been obtained in Example 8, at room temperature
  2. temperaturethe mixture was heated
  3. temperaturerefluxed for 30 minutes
  4. washwashed with ether (100 mL)
  5. customthe precipitated crystal was separated by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-346e52ea0d5b4c46b5f12bc41e1282ed
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Reaction notes

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