Sodium Chloride → 7-(2,3-Dihydroxypropyl)-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-one
Reaction equation
[CH2:1]([C:4]1[C:5]([O:16][CH3:17])=[CH:6][C:7]2[CH2:12][O:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]=2[CH:15]=1)[CH:2]=[CH2:3].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:39]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].[Cl-].[Na+].C(O)(C)(C)C.[OH2:89]>>[OH:89][CH:2]([CH2:3][OH:39])[CH2:1][C:4]1[C:5]([O:16][CH3:17])=[CH:6][C:7]2[CH2:12][O:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]=2[CH:15]=1Participants
Reactant 5
Product 1
Procedure
160 mg of 7-allyl-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-one was dissolved in 20 ml of t-butanol-water (1:1). Thereafter, 0.96 g of AD-mix-β was added to the reaction solution, and the obtained mixture was then stirred at room temperature overnight. Thereafter, 1.03 g of sodium sulfite was added to the reaction solution while cooling on ice, and the obtained mixture was stirred at room temperature for 1 hour. A saturated sodium chloride aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 280 mg of 7-(2,3-dihydroxypropyl)-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-one. This compound was used in the following reaction without further purification.
Workup
- temperaturewhile cooling on ice
- stirringthe obtained mixture was stirred at room temperature for 1 hour
- extractionfollowed by extraction with methylene chloride
- dry with materialThe extract was dried over magnesium sulfate
- concentrationconcentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-dabb798d85d043bfb81e5c228c82cbc9
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538123B2
Reaction notes
Loading…