HCID 89601667, compound → HCID 89601660, compound

HRID 570908Notes

Reaction equation

HRID 570908 reaction equation
[C:1]([N:4]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:5]1[CH2:10][C:9]([CH2:11][O:12]CC2C=CC=CC=2)=[N:8][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]1=[O:27])(=[O:3])[CH3:2]>CCO.[Pd]>[C:1]([N:4]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:5]1[CH2:10][C:9]([CH2:11][OH:12])=[N:8][N:7]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C:6]1=[O:27])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 89601667HCID 89601667, compound

Product 1

HCID 89601660HCID 89601660, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl 4-[acetyl(tert-butoxycarbonyl)amino]-6-(benzyloxymethyl)-3-oxo-5H-1,2,4-triazine-2-carboxylate (38.0 g, 79.7 mmol) in EtOH (400 mL) under argon atmosphere was added palladium on charcoal (dry, 5 wt % Pd, 8.00 g). The reaction mixture was purged with hydrogen and heated to 60° C. At this temperature, the reaction mixture was stirred 24 h under H2-atmosphere (approx. 1 atm). The mixture was purged with argon and then filtered using a short plug of silica gel followed by rinsing with additional EtOAc. Evaporation of the solvent furnished the desired product as a sticky oil. LCMS (Method I) RT 1.57 min. [M+H]+ 387.

Workup

  1. customThe reaction mixture was purged with hydrogen
  2. customThe mixture was purged with argon
  3. filtrationfiltered
  4. washby rinsing with additional EtOAc
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-63166589ed11471691dfce4ca6ade685
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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