HRID56831

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID12734

Diisopropylcarbodiimide

C7H14N2

HCID233272

Benzoic acid, 4-amino-, 1,1-dimethylethyl ester

C11H15NO2

结构：COc1cn(C(CC2CCC(O[Si](C)(C)C(C)(C)C)CC2)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N

HCID131736945

未命名化合物

PRODUCTS

生成物

结构：COc1cn(C(CC2CCC(O[Si](C)(C)C(C)(C)C)CC2)C(=O)Nc2ccc(C(=O)OC(C)(C)C)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N

HCID131736946

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

400 mg (734 μmol) of 3-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoic acid (mixture of two racemic diastereomers), 142 mg (734 μmol) of tert-butyl 4-aminobenzoate, 104 mg (734 μmol) of Oxima and 114 μl (734 μmol) of DIC in 7.3 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (40 g cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient). Yield: 341 mg (64% of theory)

WORKUP

后处理

customThe crude product was purified by flash chromatography (40 g cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-fdb78eefe36c4704be0973c457b34e99
来源数据集: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09434690B2
来源说明: uspto-grants-2016_09

反应 SMILES

[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH:16]([N:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[C:35]#[N:36])=[CH:22][C:21]2=[O:37])[C:17]([OH:19])=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:38][C:39]1[CH:51]=[CH:50][C:42]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[CH:41][CH:40]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][CH:16]([N:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[C:35]#[N:36])=[CH:22][C:21]2=[O:37])[C:17]([NH:38][C:39]2[CH:51]=[CH:50][C:42]([C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])=[CH:41][CH:40]=2)=[O:19])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]