Lithium Hydroxide → (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylate

HRID 643158Notes

Reaction equation

HRID 643158 reaction equation
[Li+].[OH-].[O:3]=[C:4]1[C:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C@@H:23]([C:41]([O:43]C)=[O:42])[CH2:24][C:25]3[CH:30]=[C:29]([CH3:31])[C:28]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:27]([CH3:40])[CH:26]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1>O.C1COCC1>[O:3]=[C:4]1[C:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C@@H:23]([C:41]([OH:43])=[O:42])[CH2:24][C:25]3[CH:26]=[C:27]([CH3:40])[C:28]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:29]([CH3:31])[CH:30]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68676170HCID 68676170, compound

Product 1

HCID 68675026(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 38 mg (1.60 mmol) LiOH in 50 mL water was added to a solution of 600 mg (1.06 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylate in 30 mL THF and the reaction mixture was stirred for 1 h at RT. The organic solvent was eliminated i.vac., the aqueous residue was diluted with 50 mL water and acidified with 1 M HCL. The precipitate formed was filtered off, washed with 10 mL water and dried at 50° C.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with 10 mL water
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-46b54d089d31472d867be7a3c574f0ee
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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