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(5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)(tert-butoxycarbonyl)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate → (5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627185
笔记
打印预览

反应方程式

HRID 627185 反应方程式
[CH2:1]([O:8][N:9](C(OC(C)(C)C)=O)[C@H:10]1[CH2:15][N:14]([C:16]([O:18][CH2:19][CH:20]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH:13]([C:33](=[O:35])[NH2:34])[C:12]([CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH2:1]([O:8][NH:9][C@H:10]1[CH2:15][N:14]([C:16]([O:18][CH2:19][CH:20]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[C:27]3[C:32]2=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:17])[CH:13]([C:33](=[O:35])[NH2:34])[C:12]([CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参与物实验过程后处理来源与证据反应笔记

参与物

4

反应物 1

HCID 124012978(5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)(tert-butoxycarbonyl)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate2 次

产物 1

HCID 89851827(5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1 (2H)-carboxylate收率 95%

试剂、催化剂与溶剂 2

HCID 10421208溴化锌催化剂
HCID 6344
二氯甲烷
溶剂
2 次

实验过程

To a solution of (5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)(tert-butoxycarbonyl)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 161, 1.19 g, 1.67 mmol) in DCM (20 mL) at room temperature was added zinc bromide (1.502 g, 6.67 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate and. The aqueous wash was extracted three to four times more with DCM. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound (0.970 g, 95%) as an off white foam.

后处理

  1. washwashed with saturated sodium bicarbonate
  2. washThe aqueous wash
  3. extractionwas extracted three to four times more with DCM
  4. washThe organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

来源与证据

ORD记录
ord-c0c0a1736e004d25b82975e9604f567c
来源数据集
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09309245B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记