HCID 10248693, compound → 3-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 2113042Notes

Reaction equation

HRID 2113042 reaction equation
C(OC([NH:11][C:12]1[C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([CH3:18])=[CH:16][CH:17]=1)=O)C1C=CC=CC=1>C(O)C.O>[NH2:11][C:12]1[C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([CH3:18])=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 10248693HCID 10248693, compound

Product 1

HCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneYield 80.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To tert-butyl 2-[3-{[(benzyloxy)carbonyl]amino}-6-methyl-2-oxo-1(2H)-pyridinyl]acetate (6.19 g, 16.6 mmol) in the reactor a mixture of 4:1 ethanol/water (77 mL) was added and degassed with argon for several minutes. During degassing Pd(OH)2 (0.613 g) was added and subjected to catalytic hydrogenation in the reactor containing a hydrogenating agent under the conditions: p(H2)=100 psi, t=2 h. The reaction mixture was filtered through Celite and the solvent evaporated under reduced pressure. To obtain a solid ethanol was added to the resulting material several times and the azeotropic mixture with water was distilled under reduced pressure to give 3.18 g (13.4 mmol) of a grey compound.

Workup

  1. additionwas added
  2. customdegassed with argon for several minutes
  3. customDuring degassing Pd(OH)2 (0.613 g)
  4. additionwas added
  5. additioncontaining a hydrogenating agent under the conditions
  6. customp(H2)=100 psi, t=2 h
  7. filtrationThe reaction mixture was filtered through Celite
  8. customthe solvent evaporated under reduced pressure
  9. customTo obtain a solid ethanol
  10. additionwas added to the resulting material several times
  11. distillationthe azeotropic mixture with water was distilled under reduced pressure

Sources & evidence

ORD record
ord-202cd8fd3eee4b4abc3728b39d6674a9
Source dataset
uspto-grants-2009_04
Patent number
US07524871B2

Reaction notes

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