Methanol → [(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]methanol
反应方程式
C([O:8][CH2:9][C@@H:10]1[N:15]2[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([NH2:26])[C:17]=3[N:27]=[C:14]2[CH2:13][O:12][CH2:11]1)C1C=CC=CC=1.CO.C(Cl)(=O)C>[Pd].C(Cl)(Cl)Cl>[NH2:26][C:18]1[C:17]2[N:27]=[C:14]3[CH2:13][O:12][CH2:11][C@H:10]([CH2:9][OH:8])[N:15]3[C:16]=2[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1参与物
反应物 3
产物 1
试剂、催化剂与溶剂 2
实验过程
(11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (4.5 g, 12 mmol) was added to a mixture of methanol (177 mL) and acetyl chloride (1.3 mL, 19 mmol) in a pressure bottle. Palladium on carbon (10%, 900 mg) was then added and the reaction mixture was shaken under H2 at 48 PSI (3.3×105 Pa). After 4 days, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with methanol and the combined filtrates were treated with 2 mL of 50% aqueous NaOH solution and the mixture was concentrated under reduced pressure to afford an oily solid. Chromatography (SiO2, 0-30% CMA/CHCl3) afforded an oil that was concentrated with acetonitrile to give 1.6 g of [(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]methanol as a tan solid.
后处理
- filtrationthe reaction mixture was filtered through a pad of CELITE
- filtrationfilter agent
- washThe pad was rinsed with methanol
- additionthe combined filtrates were treated with 2 mL of 50% aqueous NaOH solution
- concentrationthe mixture was concentrated under reduced pressure
- customto afford an oily solid
- concentrationwas concentrated with acetonitrile
来源与证据
- ORD记录
- ord-f0c7af29302f4aa9b3267b70f8dfb5a0
- 来源数据集
- uspto-grants-2011_10
- 专利号
- US08034938B2
反应笔记
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