Methanol → (R)-4-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)pentyl acetate
Reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[NH2:15][C@H:16]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:17][OH:18].CO.C(Cl)Cl.[C:28](Cl)(=[O:30])[CH3:29]>>[C:28]([O:18][CH2:17][C@H:16]([N:15]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:30])[CH3:29]Participants
Conditions
- Temperature
- 50 °C
Procedure
Into a round bottom flask was combined 5-nitro-isochromen-1-one (5.50 g, 0.0259 mol), (R)-2-amino-4-methylpentan-1-ol (6.07 g, 0.0518 mol) and methanol (160 mL, 4.1 mol). The mixture was heated at reflux for 3 hours. The mixture was allowed to cool, reduced in vacuo and dried on high vacuum for approximately 1 hour. methylene chloride (200 mL, 3 mol) and acetyl chloride (4.1 g, 0.052 mol) were added and the mixture was heated at 50° C. for 3 hours. The resulting solution was reduced in vacuo and purified. The mixture was purified by column chromatography using a methanol:methylene chloride (0-3%) gradient. The combined pure fractions were reduced in vacuo to yield the title compound as a dark yellow solid which was taken to the next step without further purification.
Workup
- customInto a round bottom flask was combined
- temperatureThe mixture was heated
- temperatureat reflux for 3 hours
- temperatureto cool
- customdried on high vacuum for approximately 1 hour
- custompurified
- customThe mixture was purified by column chromatography
Sources & evidence
- ORD record
- ord-9ebec220b5e1470896911740cf4a5378
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816371B2
Reaction notes
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