Hydrochloric Acid → (S)-3-Quinolin-3-yl-3-(5-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl-pentanoylamino)-propionic acid

HRID 1837877Notes

Reaction equation

HRID 1837877 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C@H:18]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:19][C:20]([O:22]CC)=[O:21])=[O:16].[Li+].[OH-].Cl>CCO>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[C:25]([C@@H:18]([NH:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][NH:9][C:10]=3[N:1]=2)[CH2:19][C:20]([OH:22])=[O:21])[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 60105751Ethyl 3-(5-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)pentanoylamino)-3(S)-(quinolin-3-yl)-propionate

Product 1

HCID 10320601(S)-3-Quinolin-3-yl-3-(5-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl-pentanoylamino)-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ester 5-8 (145 mg, 0.320 mmol) was dissolved in 1 mL EtOH and treated with 1N LiOH (352 mL, 0.35 mmol) and stirred at room temperature overnight. The reaction solution was neutralized with 1N HCl (352 mL), evaporated, and purified by chromatography on silica gel (60% 20:1:1 EtOH/NH4OH/H2O—40% EtOAc) to afford 5-9 as a white solid.

Workup

  1. customevaporated
  2. custompurified by chromatography on silica gel (60% 20:1:1 EtOH/NH4OH/H2O—40% EtOAc)

Sources & evidence

ORD record
ord-1f4a1886d3ba4d3b89a28b2b036ff887
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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