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

HRID 379221Notes

Reaction equation

HRID 379221 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-4d0e9b0c18d7494fb335a0703e4e2329
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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