Trifluoroacetic acid → 3-[4-(1,2,5,6-Tetrahydropyridin-4-yl)phenyl]butyryl-beta-alanine

HRID 265875Notes

Reaction equation

HRID 265875 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][NH:9][C:10](=[O:34])[CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH:22](O)[CH2:21]2)=[CH:16][CH:15]=1)[CH3:13])(C)(C)[CH3:2].C(O)(C(F)(F)F)=[O:37]>C(Cl)Cl>[CH2:1]([OH:5])[CH3:2].[NH4+:9].[OH-:37].[OH2:5].[NH:23]1[CH2:24][CH2:25][C:20]([C:17]2[CH:16]=[CH:15][C:14]([CH:12]([CH3:13])[CH2:11][C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:35])=[O:5])=[O:34])=[CH:19][CH:18]=2)=[CH:21][CH2:22]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 190341073-[4-(N-BOC-Hydroxypiperidin-4-yl)phenyl]butyryl-beta-alanine-tert-butyl Ester

Product 2

HCID 190341263-[4-(1,2,5,6-Tetrahydropyridin-4-yl)phenyl]butyryl-beta-alanineHCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 12-5 (120 mg, 0.25 mmoles), CH2Cl2 (1.0 mL), and TFA (1.0 mL) was stirred at ambient temperature for 4.0 hours and then concentrated with azeotropic removal of the excess TFA. Flash chromatography (silica, 10/1/1 ethanol/NH4OH/H2O/gave 12-6 as a white solid. Rf 0.13 (10/1/1 ethanol/NH4OH/H2O).

Workup

  1. concentrationconcentrated with azeotropic removal of the excess TFA

Sources & evidence

ORD record
ord-2f61261852b04d12a5b35c65d63c6c77
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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