Potassium Hydroxide → HCID 59314201, compound

HRID 1047738Notes

Reaction equation

HRID 1047738 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17]([C:19]2[C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:14][C:13]2[CH:12]=[N:11][C:10]([CH3:15])=[CH:9][C:8]=2[CH2:7]1)=[O:5])C.[OH-].[K+]>CCO.O>[CH3:15][C:10]1[N:11]=[CH:12][C:13]2[CH2:14][C:6]([NH:16][C:17]([C:19]3[C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)=[O:18])([C:4]([OH:5])=[O:3])[CH2:7][C:8]=2[CH:9]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59314194HCID 59314194, compound

Product 1

HCID 59314201HCID 59314201, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The mixture of 3-methyl-6-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester (82) and KOH (1 g, 17.9 mmol) in EtOH (5 mL) and water (0.3 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 3 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl dropwise until no more precipitate came out of the water. After the filtration, the solid is purified by HPLC to give a pure product (83) as colorless oil (20 mg, 22%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (20 mL)
  6. filtrationAfter the filtration
  7. customthe solid is purified by HPLC

Sources & evidence

ORD record
ord-99c4c902301845be86cdfdabb2f49a27
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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