Lithium hydroxide, monohydrate → (R)-3-(7-Methyl-1H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)propanoic acid

HRID 501955

Reaction equation

HRID 501955 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@H:21]([CH2:26][C:27]3[CH:28]=[C:29]4[C:33](=[C:34]([CH3:36])[CH:35]=3)[NH:32][N:31]=[CH:30]4)[C:22]([O:24]C)=[O:23])=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.O.[OH-].[Li+]>CO.O1CCCC1.O>[CH3:36][C:34]1[CH:35]=[C:27]([CH2:26][C@@H:21]([O:20][C:18]([N:15]2[CH2:14][CH2:13][CH:12]([C:11]3[C:2](=[O:1])[NH:3][C:4]4[C:9]([CH:10]=3)=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:17][CH2:16]2)=[O:19])[C:22]([OH:24])=[O:23])[CH:28]=[C:29]2[C:33]=1[NH:32][N:31]=[CH:30]2

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59424336(R)-1-Methoxy-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 59424312(R)-3-(7-Methyl-1H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)propanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-1-methoxy-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (1.20 g, 2.46 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL) at 0° C. was added a precooled solution of lithium hydroxide monohydrate (309 mg, 3.0 equiv) in water (10 mL). After 2 h, the reaction was concentrated under high vaccuum (<25° C.). The resulting residue was dissolved in water (20 mL), cooled to 0° C., and acidified to ca. pH 2 with 1 N hydrochloric acid. The suspension was maintained at 0° C. for 1 h, filtered, and the solid washed with cold water. The resulting white solid was air dried and then dried under high vacuum overnight to give 1.04 g (89%) as a white solid. Mass spec.: 475.30 (MH)+.

Workup

  1. concentrationthe reaction was concentrated under high vaccuum (<25° C.)
  2. dissolutionThe resulting residue was dissolved in water (20 mL)
  3. temperatureThe suspension was maintained at 0° C. for 1 h
  4. filtrationfiltered
  5. washthe solid washed with cold water
  6. customdried
  7. customdried under high vacuum overnight
  8. customto give 1.04 g (89%) as a white solid

Sources & evidence

ORD record
ord-fc096ab435514d8d89557808b6c67626
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Linked notes

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