Hydrochloric Acid → HCID 53491904, compound

HRID 1801060Notes

Reaction equation

HRID 1801060 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:30])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:25]([OH:27])=[O:26])([CH3:24])[CH3:23])[CH:16]=1)[C:11]([CH3:29])([CH3:28])[CH2:10]2)=[O:4].O.[OH-].[Li+].O.Cl>CO.O1CCCC1>[C:25]([C:22]([NH:21][C:17]1[CH:16]=[C:15]([CH:12]2[C:11]([CH3:28])([CH3:29])[CH2:10][C:9]3[C:14](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([Cl:30])[CH:8]=3)[NH:13]2)[CH:20]=[CH:19][CH:18]=1)([CH3:23])[CH3:24])([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53491902HCID 53491902, compound

Product 1

HCID 53491904HCID 53491904, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (100 mg, 0.23 mmol), lithium hydroxide hydrate (98 mg, 2.3 mmol), water (0.5 mL) in methanol (1 mL) and tetrahydrofuran (5 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford an oil residue. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (24 mg, 25%) as a white solid: LC/MS m/e calcd for C22H25ClN2O4 (M+H)+: 417.91, observed: 417.0.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford an oil residue
  6. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

Sources & evidence

ORD record
ord-afe32364bc474a3e801d1b19cc90a3dd
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…