Trifluoroacetic acid → 4-(1,2,3,4-Tetrahydro-1,8-naphthyridin-7-yl)butanoyl-glycyl-beta-alanine

HRID 1597641Notes

Reaction equation

HRID 1597641 reaction equation
C([O:5][C:6](=[O:29])[CH2:7][CH2:8][NH:9][C:10](=[O:28])[CH2:11][NH:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][C:17]1[N:26]=[C:25]2[C:20]([CH2:21][CH2:22][CH2:23][NH:24]2)=[CH:19][CH:18]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:24]1[C:25]2[C:20](=[CH:19][CH:18]=[C:17]([CH2:16][CH2:15][CH2:14][C:13]([NH:12][CH2:11][C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:29])=[O:5])=[O:28])=[O:27])[N:26]=2)[CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 216998024-(1,2,3,4-Tetrahydro-1,8-naphthyridin-7-yl)butanoyl-glycyl-beta-alanine t-butyl ester

Product 1

HCID 216997784-(1,2,3,4-Tetrahydro-1,8-naphthyridin-7-yl)butanoyl-glycyl-beta-alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 19-9 (69 mg, 0.17 mmol) was dissolved in 1 mL CH2Cl2 at 0° C., 1 mL TFA was added, and the reaction was warmed to ambient temperature for 6 hr. After concentrating and azeotroping with toluene, flash chromatography (silica, 7:20:1:1 EtOAc/EtOH/H2O/NH4OH) provided 19-10 as a white solid.

Workup

  1. concentrationAfter concentrating
  2. customazeotroping with toluene, flash chromatography (silica, 7:20:1:1 EtOAc/EtOH/H2O/NH4OH)

Sources & evidence

ORD record
ord-f36972228eff4725857d6f409bf52ee5
Source dataset
uspto-grants-2001_09
Patent number
US06294549B1

Reaction notes

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