HRID2082629

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6101

4-Methylbenzenesulfonic acid

C7H8O3S

结构：CCC1C=C(C)C(F)C(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4ccc5cc(O[Si](C)(C)C(C)(C)C)ccc5c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC

HCID57108327

未命名化合物

PRODUCTS

生成物

结构：CCC1C=C(C)C(F)C(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4ccc5cc(O)ccc5c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC

HCID131717793

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a stirred solution of 17-ethyl-20-fluoro-1,14-dihydroxy-12-[2'-(4"-(6'"-tert-butyldimethylsilyloxynaphth-2-yloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (73 mg, 0.07 mmol) in CH2Cl2 (2 mL) was added a solution of p-toluenesulfonic acid in methanol (2 mL, 10% solution). The flask is capped and the mixture stirred 4 hours. The reaction is quenched with saturated aqueous NaHCO3 and extracted 4× with CH2Cl2. The organic extracts are combined and dried over anhydrous Na2SO4. The mixture is filtered and concentrated in vacuo. The product is isolated by preparative TLC on silica gel to afford the title compound.

WORKUP

后处理

customThe flask is capped
customThe reaction is quenched with saturated aqueous NaHCO3
extractionextracted 4× with CH2Cl2
dry with materialdried over anhydrous Na2SO4
filtrationThe mixture is filtered
concentrationconcentrated in vacuo
customThe product is isolated by preparative TLC on silica gel

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1c01a3b8e9d64f16b1aa3b62136467f0
来源数据集: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05189042
来源说明: uspto-grants-1993_02

反应 SMILES

[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:72])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][C:52]3[CH:61]=[CH:60][C:59]4[C:54](=[CH:55][CH:56]=[C:57]([O:62][Si](C(C)(C)C)(C)C)[CH:58]=4)[CH:53]=3)[CH:47]([O:70][CH3:71])[CH2:46]2)[CH:7]([CH3:73])[CH:6]([OH:74])[CH2:5][C:4]1=[O:75])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CO>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:72])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][C:52]3[CH:61]=[CH:60][C:59]4[C:54](=[CH:55][CH:56]=[C:57]([OH:62])[CH:58]=4)[CH:53]=3)[CH:47]([O:70][CH3:71])[CH2:46]2)[CH:7]([CH3:73])[CH:6]([OH:74])[CH2:5][C:4]1=[O:75])[CH3:2]