Trifluoroacetic acid → 2-(3-(((Benzyloxy)carbonyl)amino)-2-oxopyridin-1(2H)-yl)acetic acid

HRID 1057755Notes

Reaction equation

HRID 1057755 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C:9]1=[O:25])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:18]([O:17][C:15]([NH:14][C:10]1[C:9](=[O:25])[N:8]([CH2:7][C:6]([OH:26])=[O:5])[CH:13]=[CH:12][CH:11]=1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70027044(3-Benzyloxycarbonylamino-2-oxo-2h-pyridin-1-yl)acetic acid tert-butyl ester

Product 1

HCID 186721592-(3-(((Benzyloxy)carbonyl)amino)-2-oxopyridin-1(2H)-yl)acetic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)acetic acid tert-butyl ester (0.485 g, 1.35 mmol) was stirred in a 1:1 mixture of trifluoroacetic acid and CH2Cl2 at 23° C. for 1 h. The volatiles were then removed under reduced pressure and the residue was triturated with Et2O (40 mL). The resulting solid was filtered through a medium frit, washed with Et2O (20 mL) and air-dried to give the title intermediate (0.315 g, 77%): mp=171-173° C.; 1H NMR (DMSO-d6) δ 4.67 (s, 2H), 5.15 (s, 2H), 6.28 (t, 1H, J=7.1), 7.29-7.43 (m, 7H), 7.85 (dd, 1H, J=7.4, 1.7), 8.47 (s, 1H).

Workup

  1. customThe volatiles were then removed under reduced pressure
  2. customthe residue was triturated with Et2O (40 mL)
  3. filtrationThe resulting solid was filtered through a medium frit
  4. washwashed with Et2O (20 mL)
  5. customair-dried

Sources & evidence

ORD record
ord-b00c24daccb445e58ed3711de91b1dd6
Source dataset
uspto-grants-2003_02
Patent number
US06514997B2

Reaction notes

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