Ethanol → HCID 117667724, compound

HRID 712737Notes

Reaction equation

HRID 712737 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][O:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[N:16][C:17]3[N:18]([C:24](=[O:26])[NH2:25])[CH2:19][CH2:20][CH2:21][C:22]=3[CH:23]=2)[CH:13]=1)C.[Li+].[OH-].CCO>O>[C:24]([N:18]1[C:17]2[N:16]=[CH:15][C:14]([C:12]3[CH:13]=[C:8]([CH2:7][O:6][CH2:5][C:4]([OH:27])=[O:3])[CH:9]=[N:10][CH:11]=3)=[CH:23][C:22]=2[CH2:21][CH2:20][CH2:19]1)(=[O:26])[NH2:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 117667342HCID 117667342, compound

Product 1

HCID 117667724HCID 117667724, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[5-(8-Carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-ylmethoxy]-acetic acid ethyl ester (1.0 g, 2.7 mmol) and LiOH (0.10 g, 4.2 mmol) are mixed in H2O (10 mL) and EtOH (10 mL) and stirred at room temperature overnight. The reaction mixture is concentrated under vacuum and treated with 1 N HCl, and ethyl acetate. The organic layer is concentrated to give [5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-ylmethoxy]-acetic acid (0.80 g).

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. additiontreated with 1 N HCl, and ethyl acetate
  3. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-57425d1706e64cef85742d5c73c920a4
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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