Benzyl Alcohol → 3-benzyloxycarbonylamino-6-methyl-2-pyridinone
Reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[OH:18][C:19]1[C:24](C(O)=O)=[CH:23][CH:22]=[C:21]([CH3:28])[N:20]=1.C([N:31]([CH2:34]C)CC)C.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1>[CH2:36]([O:43][C:34]([NH:31][C:24]1[C:19](=[O:18])[NH:20][C:21]([CH3:28])=[CH:22][CH:23]=1)=[O:8])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1Participants
6
Procedure
Diphenylphosphoryl azide (11.9 mL, 55 mmol) was added to a solution of 2-hydroxy-6-methylpyridine-3-carboxylic acid (7.65 g, 50 mmol) and triethylamine (7.7 mL, 55 mmol) in dry dioxane (100 mL) and the resulting solution was heated to reflux. After 16 h additional triethylamine (7.7 mL, 55 mmol) and benzyl alcohol (5.7 mL, 50 mmol) were added and the solution was refluxed for a further 24 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride (200 mL) and brine (100 mL), and acidified to pH 1 with 10% HCl. The organic layer was washed with saturated NaHCO3 (2×100 mL), brine (100 mL), dried over Na2SO4, and filtered.
Workup
- temperaturethe resulting solution was heated to reflux
- temperaturethe solution was refluxed for a further 24 h
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue was partitioned between methylene chloride (200 mL) and brine (100 mL)
- washThe organic layer was washed with saturated NaHCO3 (2×100 mL), brine (100 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-2180bd3fac2a4ff9a1e0b4ee4aa998ed
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420397B1
Reaction notes
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