HRID216918

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID44118572

{4-[(Methanesulfonyl)oxy]phenyl}boronic acid

C7H9BO5S

结构：CC(C)(C)OC(=O)NC1(C(=O)N[C@@H](Cc2ccc(I)cc2)C(N)=O)CCOCC1

HCID59568595

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)NC1(C(=O)N[C@@H](Cc2ccc(-c3ccc(OS(C)(=O)=O)cc3)cc2)C(N)=O)CCOCC1

HCID59568621

未命名化合物

收率 72%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

CONDITIONS

反应条件

温度: 85 °C

PROCEDURE

实验过程

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 300 mg) in acetonitrile (7 mL) under nitrogen was treated with 4-(methylsulfonyloxy)phenylboronic acid (125 mg) followed by aqueous sodium carbonate (2M, 0.58 mL). Nitrogen was bubbled through the mixture and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added. The mixture was stirred at 85° C. for 25 h. The solvent was partially evaporated and then purified by chromatography on silica using ethyl acetate 50-100% isohexane as eluent to afford the sub-titled compound as a white solid (234 mg).

WORKUP

后处理

customNitrogen was bubbled through the mixture and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg)
additionwas added
customThe solvent was partially evaporated
custompurified by chromatography on silica

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4aabba31b8344cb68096fc3d624b8591
来源数据集: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08193239B2
来源说明: uspto-grants-2012_06

反应 SMILES

[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH3:30][S:31]([O:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:30][S:31]([O:34][C:35]1[CH:36]=[CH:37][C:38]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C@H:3]([NH:12][C:13]([C:15]3([NH:21][C:22]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:28])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:14])[C:2]([NH2:1])=[O:29])=[CH:6][CH:7]=2)=[CH:39][CH:40]=1)(=[O:33])=[O:32]