HRID658253

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID9886157

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

C10H15F6N6OP

结构：COCCCc1cc(CNC2CC2)cc(O[Si](C)(C)C(C)(C)C)c1

HCID57956095

未命名化合物

结构：Cc1cc(Cl)c(OCCOc2ccc([C@H]3CCN(C(=O)OC(C)(C)C)C[C@@H]3C(=O)O)cc2)c(Cl)c1

HCID59234216

未命名化合物

PRODUCTS

生成物

结构：COCCCc1cc(CN(C(=O)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2c2ccc(OCCOc3c(Cl)cc(C)cc3Cl)cc2)C2CC2)cc(O[Si](C)(C)C(C)(C)C)c1

HCID86639853

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3283

Diethyl Ether

C4H10O

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of (3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acid (piperidine acid 1) (1 eq) and N-[3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl]cyclo-propanamine (amine 1) (1.8 eq.) in DCM (0.15 M) was added HATU (1.5 eq.) and Hunig's base (3 eq.). After stirring for 18 hr at rt, the reaction was diluted with ether. The organic extract was washed three times with 1 N aqueous HCl, water, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex) to afford the title compound as an oil.

WORKUP

后处理

extractionThe organic extract
washwas washed three times with 1 N aqueous HCl, water, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-43dc98af8a2b401194bb63835ec3fb9c
来源数据集: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08076359B2
来源说明: uspto-grants-2011_12

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[C@@H:10]([C:33]([OH:35])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si:36]([O:43][C:44]1[CH:45]=[C:46]([CH:52]=[C:53]([CH2:55][CH2:56][CH2:57][O:58][CH3:59])[CH:54]=1)[CH2:47][NH:48][CH:49]1[CH2:51][CH2:50]1)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOCC>[Si:36]([O:43][C:44]1[CH:45]=[C:46]([CH:52]=[C:53]([CH2:55][CH2:56][CH2:57][O:58][CH3:59])[CH:54]=1)[CH2:47][N:48]([CH:49]1[CH2:51][CH2:50]1)[C:33]([C@@H:10]1[C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:35])([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38]