HCID 89601660, compound → HCID 89601756, compound

HRID 570909Notes

Reaction equation

HRID 570909 reaction equation
[C:1]([N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:5]1[CH2:10][C:9]([CH2:11][OH:12])=[N:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[C:1]([N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:5]1[CH2:10][C:9]([CH:11]=[O:12])=[N:8][N:7]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 89601660HCID 89601660, compound

Product 1

HCID 89601756HCID 89601756, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of tert-butyl 4-[acetyl(tert-butoxycarbonyl)amino]-6-(hydroxymethyl)-3-oxo-5H-1,2,4-triazine-2-carboxylate (3.01 g, 7.78 mmol) in CHCl3 (47 mL) was added manganese(IV) oxide (7.96 g, 77.8 mmol) and the obtained mixture was heated under reflux for 20 h. The obtained reaction mixture was filtered over Celite and followed by rinsing with 20% MeOH/CHCl3. Removal of the solvent in vacuo furnished the desired product as a sticky oil which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) 1.43 (s, 9H), 1.52 (s, 9H), 2.48 (s, 3H), 4.26 (dAB, 1H), 4.34 (dAB, 1H), 9.58 (s, 1H).

Workup

  1. temperaturethe obtained mixture was heated
  2. temperatureunder reflux for 20 h
  3. customThe obtained reaction mixture
  4. filtrationwas filtered over Celite
  5. washby rinsing with 20% MeOH/CHCl3
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-6464eaf558194bf2802ef859966d5da0
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

Loading…