(S)-2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester → (S)-2-(3-Amino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester

HRID 2422686Notes

Reaction equation

HRID 2422686 reaction equation
[C:1]([O:5][C:6](=[O:28])[C@@H:7]([N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16]C(OCC2C=CC=CC=2)=O)[C:11]1=[O:27])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:28])[C@@H:7]([N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:11]1=[O:27])[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 57648851(S)-2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester

Product 1

HCID 60129041(S)-2-(3-Amino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester (2.48 g, 6.43 mmol) in a mixture of MeOH (15 mL) and EtOAc (15 mL) was added 10% Pd/C (250 mg). The mixture was degassed and stirred at room temperature for 90 minutes under an atmosphere of hydrogen (balloon pressure). The reaction mixture was filtered through a short pad of silica which was then flushed with MeOH. The combined filtrates were evaporated under reduced pressure to afford the title compound as a white solid (1.62 g, 100%); 1H NMR (400 MHz, CDCl3) δ 0.91 (3H, t), 1.44 (9H, s), 1.91 (1H, m), 2.21 (1H, m), 4.24 (2H, br s), 5.50 (1H, dd), 6.11 (1H, t), 6.53 (1H, d), 6.77 (1H, d)

Workup

  1. customThe mixture was degassed
  2. filtrationThe reaction mixture was filtered through a short pad of silica which
  3. customwas then flushed with MeOH
  4. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-6f5a0a3b650846f0a48c24545687ac40
Source dataset
uspto-grants-2011_06
Patent number
US07960415B2

Reaction notes

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