HRID339903

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

结构：CC(C)(C)N1CC=C(OS(=O)(=O)C(F)(F)F)CC1

HCID18694292

未命名化合物

结构：CC1(C)OC(N[C@@H](CCO[Si](C)(C)C(C)(C)C)c2ccccc2F)=NS(=O)(=O)C1c1ccc(B2OC(C)(C)C(C)(C)O2)cc1

HCID178431682

未命名化合物

PRODUCTS

生成物

结构：CC1(C)OC(N[C@@H](CCO[Si](C)(C)C(C)(C)C)c2ccccc2F)=NS(=O)(=O)C1c1ccc(C2=CCN(C(C)(C)C)CC2)cc1

HCID178431684

未命名化合物

收率 67.8%

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd]

催化剂HCID6505921

未命名化合物

结构：CC(C)(C)P([C]1[CH][CH][CH][CH]1)C(C)(C)C.[Fe].c1ccc([C]2[C](c3ccccc3)[C](c3ccccc3)[C](c3ccccc3)[C]2c2ccccc2)cc1

催化剂HCID178454872

未命名化合物

溶剂HCID21886435

1,4-Dioxane--water (1/1)

C4H10O3

CONDITIONS

反应条件

温度: 62 °C

PROCEDURE

实验过程

To a solution of [(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propyl]-{6,6-dimethyl-4,4-dioxo-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-2-yl}amine (300 mg), trifluoromethanesulfonic acid 1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl ester (208 mg) and cesium carbonate (519 mg) in 3:1 dioxane/water (4 ml) were added Pd(dba)2 (31 mg) and CTC-Q-Phos (75 mg), and the mixture was stirred at 62° C. for 40 min. After dilution with ethyl acetate, the mixture was washed with water, dried using a kieselguhr cartridge and concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (207 mg) with a molecular weight of 658.0 g/mol (C35H52FN3O4SSi).

WORKUP

后处理

washAfter dilution with ethyl acetate, the mixture was washed with water
customdried
concentrationconcentrated
customThis was followed by purification by column chromatography (ethyl acetate/heptane)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-06d5ff6be70a409ebd1cd6a503bee4d9
来源数据集: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08895547B2
来源说明: uspto-grants-2014_11

反应 SMILES

[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:44])([CH3:43])[CH:23]([C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:45]([N:49]1[CH2:54][CH:53]=[C:52](OS(C(F)(F)F)(=O)=O)[CH2:51][CH2:50]1)([CH3:48])([CH3:47])[CH3:46].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.C1C=CC([C]2[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C]2C2C=CC=CC=2)=CC=1.[Fe].O1CCOCC1.O>[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:44])([CH3:43])[CH:23]([C:28]2[CH:29]=[CH:30][C:31]([C:52]3[CH2:51][CH2:50][N:49]([C:45]([CH3:46])([CH3:47])[CH3:48])[CH2:54][CH:53]=3)=[CH:32][CH:33]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]