Hydrochloric Acid → 1-(2,4-Dimethoxybenzyl)-7-(2-(r)-hydroxymethyl-piperidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

HRID 1867938Notes

Reaction equation

HRID 1867938 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]3[CH2:22][OH:23])[N:14]=2)[C:9](=[O:24])[C:8]([C:25]([O:27]CC)=[O:26])=[CH:7]1.[OH-].[Li+].Cl.O>C(O)C>[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]3[CH2:22][OH:23])[N:14]=2)[C:9](=[O:24])[C:8]([C:25]([OH:27])=[O:26])=[CH:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 69030307Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-hydroxymethylpiperidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate

Product 1

HCID 690322461-(2,4-Dimethoxybenzyl)-7-(2-(r)-hydroxymethyl-piperidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of EXAMPLE 5A (2.3 g) and 0.1M lithium hydroxide (90 mL) in ethanol (110 mL) was stirred for 16 hours, adjusted to pH 3 with 1M hydrochloric acid, treated with water, and extracted with dichloromethane. The extract was concentrated, and the concentrate was recrystallized from ethyl acetate/hexanes.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe extract was concentrated
  3. customthe concentrate was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7dbd37be71d548dcbf68616a17e5e6f4
Source dataset
uspto-grants-2009_12
Patent number
US07632946B2

Reaction notes

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