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

HRID 643154Notes

Reaction equation

HRID 643154 reaction equation
[Li+].[OH-].[O:3]=[C:4]1[N:16]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C@@H:26]([C:44]([O:46]C)=[O:45])[CH2:27][C:28]3[CH:33]=[C:32]([CH3:34])[C:31]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[C:30]([CH3:43])[CH:29]=3)=[O:24])[CH2:19][CH2:18]2)[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[NH:5]1>O.C1COCC1>[O:3]=[C:4]1[N:16]([CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C@@H:26]([C:44]([OH:46])=[O:45])[CH2:27][C:28]3[CH:33]=[C:32]([CH3:34])[C:31]([O:35][CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[C:30]([CH3:43])[CH:29]=3)=[O:24])[CH2:21][CH2:22]2)[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[NH:5]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68676084HCID 68676084, compound

Product 1

HCID 68675784(R)-1-carboxy-2-(4-benzyloxy-3,5-dimethyl-phenyl)-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg (10.42 mmol) LiOH in 10 mL water was added to a solution of 2.50 g (4.11 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate in 20 mL THF and the reaction mixture was stirred for 2 h at RT. The organic solvent was removed i.vac., the aqueous residue was acidified with 2 M HCL and combined with EtOAc/DCM (2:1). The precipitate formed was filtered off and dried.

Workup

  1. customThe organic solvent was removed i.vac
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-f2b17a13313c47c0b52e14eba1936f1d
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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