HRID1852195

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID23665647

2-Methyl-2-propanol, potassium salt

C4H9KO

结构：COc1ccc2c(Cl)cc(-c3ccc(OC(C)C)cc3)nc2c1

HCID70978267

未命名化合物

$结构：CC1CC/C=C\[C@@H]2C[C@@]2(C(=O)NS(=O)(=O)C2(CF)CC2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)OC(C)(C)C)[C@H](C)C1$

HCID71005415

未命名化合物

PRODUCTS

生成物

$结构：COc1ccc2c(O[C@@H]3C[C@H]4C(=O)N[C@]5(C(=O)NS(=O)(=O)C6(CF)CC6)C[C@H]5/C=C\CCC(C)C[C@@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)N4C3)cc(-c3ccc(OC(C)C)cc3)nc2c1$

HCID86683252

未命名化合物

收率 60%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID679

Dimethyl sulfoxide

C2H6OS

PROCEDURE

实验过程

To a solution of tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-14a-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-hydroxy-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate (150 mg, 0.238 mmole) and 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline (93 mg, 0.284 mmole) in DMSO (8 mL) was added t-BuOK (133 mg, 1.19 mmol, 1 M solution in THF, 1.2 mL) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 h. The reaction mass was quenched with aqueous citric acid solution and extracted with ethyl acetate (10 mL×2). The combined organic layer was washed with water, brine solution, dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by HPLC to get 130 mg (60%) of desired compound tert-butyl (2R,6S,7R,13aS,14aR,16aS,Z)-14a-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate as white solid. MS: MS m/z 921.5 (M++1).

WORKUP

后处理

customThe reaction mass was quenched with aqueous citric acid solution
extractionextracted with ethyl acetate (10 mL×2)
washThe combined organic layer was washed with water, brine solution
dry with materialdried over anhydrous Na2SO4
customevaporated under reduced pressure
customto get crude compound
customThe crude compound was purified by HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-97fc9e4678794c3a83f96851de6ee910
来源数据集: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08957203B2
来源说明: uspto-grants-2015_02

反应 SMILES

[F:1][CH2:2][C:3]1([S:6]([NH:9][C:10]([C@@:12]23[CH2:27][C@H:26]2[CH:25]=[CH:24][CH2:23][CH2:22][CH:21]([CH3:28])[CH2:20][C@@H:19]([CH3:29])[C@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:17](=[O:38])[N:16]2[CH2:39][C@H:40]([OH:42])[CH2:41][C@H:15]2[C:14](=[O:43])[NH:13]3)=[O:11])(=[O:8])=[O:7])[CH2:5][CH2:4]1.Cl[C:45]1[C:54]2[C:49](=[CH:50][C:51]([O:55][CH3:56])=[CH:52][CH:53]=2)[N:48]=[C:47]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH:64]([CH3:66])[CH3:65])=[CH:59][CH:58]=2)[CH:46]=1.CC([O-])(C)C.[K+]>CS(C)=O>[F:1][CH2:2][C:3]1([S:6]([NH:9][C:10]([C@@:12]23[CH2:27][C@H:26]2[CH:25]=[CH:24][CH2:23][CH2:22][CH:21]([CH3:28])[CH2:20][C@@H:19]([CH3:29])[C@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35])[C:17](=[O:38])[N:16]2[CH2:39][C@H:40]([O:42][C:45]4[C:54]5[C:49](=[CH:50][C:51]([O:55][CH3:56])=[CH:52][CH:53]=5)[N:48]=[C:47]([C:57]5[CH:62]=[CH:61][C:60]([O:63][CH:64]([CH3:66])[CH3:65])=[CH:59][CH:58]=5)[CH:46]=4)[CH2:41][C@H:15]2[C:14](=[O:43])[NH:13]3)=[O:11])(=[O:7])=[O:8])[CH2:5][CH2:4]1