Trifluoroacetic acid → N-[(3-Hydroxy-2-pyridinyl)carbonyl]glycine

HRID 1430203Notes

Reaction equation

HRID 1430203 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][NH:8][C:9]([C:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:17][C:16]1[C:11]([C:9]([NH:8][CH2:7][C:6]([OH:18])=[O:5])=[O:10])=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59513077HCID 59513077, compound

Product 1

HCID 9837038N-[(3-Hydroxy-2-pyridinyl)carbonyl]glycineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(3-hydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester, 29, (0.070 g, 0.277 mmol) in CH2Cl2 (4 mL) is added TFA (1 mL). The resulting solution is stirred for 5 hours then concentrated under reduced pressure to afford 0.054 g (99% yield) of the desired compound as a colorless solid. 1H NMR (400 MHz, MeOD) δ ppm 8.09 (1H, d, J=3.3 Hz), 7.36-7.59 (2H, m), 4.08 (2H, s). HPLC-MS: m/z 197 [M+H]+.

Workup

  1. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-10477d1295454dfb9f4cc4ec3e4c2074
Source dataset
uspto-grants-2015_01
Patent number
US08940773B2

Reaction notes

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