Trifluoroacetic acid → Trifluoroacetic acid

HRID 77124Notes

Reaction equation

HRID 77124 reaction equation
C(OC([NH:8][CH2:9][C:10]1[NH:14][N:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=1)=O)(C)(C)C.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>C(Cl)Cl>[NH2:8][CH2:9][C:10]1[NH:14][N:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=1.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10468345Ethyl 3-(((tert-butoxycarbonyl)amino)methyl)-1H-1,2,4-triazole-5-carboxylate

Product 2

HCID 6422Trifluoroacetic acidYield 90%HCID 10727000Ethyl 5-(aminomethyl)-1H-1,2,4-triazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 5-((tert-butoxycarbonylamino)methyl)-1H-1,2,4-triazole-3-carboxylate (100 mg, 0.37 mmol) [Borg, S. et al., J. Org. Chem., 60:3112-3120 (1995)] was dissolved in CH2Cl2 (2 mL) and TFA (1 mL). After 1 h, this was concentrated to give ethyl 5-(aminomethyl)-1H-1,2,4-triazole-3-carboxylate, TFA (Int-XIV, 95 mg, 0.33 mmol, 90%); LCMS=171.1 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 4.45 (2 H, q, J=7.12 Hz), 4.35 (2 H, s), 1.40 (3 H, t, J=7.15 Hz).

Workup

  1. concentrationthis was concentrated

Sources & evidence

ORD record
ord-aa171cbfdae64eb08281cd0a3a3ad3e1
Source dataset
uspto-grants-2014_09
Patent number
US08835470B2

Reaction notes

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