HRID2112315

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1049

Pyridine

C5H5N

HCID16916

Chlorodimethyl sulfide

C2H5ClS

结构：CC#C[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(N(C)CCO[C@H]4CC[C@@]5(C)[C@@H](C4)C[C@@H](O)[C@@H]4[C@@H]5C[C@H](O)[C@]5(C)[C@@H]([C@H](C)CCC(=O)OC)CC[C@@H]45)cc3)C[C@@]21C

HCID131726114

未命名化合物

PRODUCTS

生成物

结构：CC#C[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(N(C)CCO[C@H]4CC[C@@]5(C)[C@@H](C4)C[C@@H](OCSC)[C@@H]4[C@@H]5C[C@H](O)[C@]5(C)[C@@H]([C@H](C)CC(C)C(=O)O)CC[C@@H]45)cc3)C[C@@]21C

HCID131726118

未命名化合物

PROCEDURE

实验过程

The compound of Example 1I is dissolved in pyridine and cooled in an ice bath; methylthiomethyl chloride (1.2 eq) is added, and the mixture is warmed to ambient temperature, then heated to 90° C. overnight. The solvents are removed in vacuo; the residue is partitioned between aqueous phosphoric acid (1N) and ethyl acetate. The organic extract is washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is purified by column chromatography.

WORKUP

后处理

temperaturecooled in an ice bath
temperatureheated to 90° C. overnight
customThe solvents are removed in vacuo
customthe residue is partitioned between aqueous phosphoric acid (1N) and ethyl acetate
extractionThe organic extract
washis washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material is purified by column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a7e36f95b60c4753b25cc7c69414f4d8
来源数据集: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07521439B2
来源说明: uspto-grants-2009_04

反应 SMILES

[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:61])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:29][N:30]([C:32]3[CH:37]=[CH:36][C:35]([C@H:38]4[CH2:55][C@@:53]5([CH3:54])[C@@H:49]([CH2:50][CH2:51][C@:52]5([OH:59])[C:56]#[C:57][CH3:58])[C@H:48]5[C:39]4=[C:40]4[C:45]([CH2:46][CH2:47]5)=[CH:44][C:43](=[O:60])[CH2:42][CH2:41]4)=[CH:34][CH:33]=3)[CH3:31])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:63])([C@@H:17]([OH:62])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH2:6][CH2:5]1.[CH3:64][S:65][CH2:66]Cl.N1C=CC=C[CH:69]=1>>[CH3:69][CH:10]([CH2:9][C@H:8]([C@@H:7]1[C@:16]2([CH3:63])[C@H:4]([C@H:3]3[C@H:19]([CH2:18][C@@H:17]2[OH:62])[C@:20]2([CH3:61])[C@@H:25]([CH2:24][C@@H:23]([O:27][CH2:28][CH2:29][N:30]([C:32]4[CH:33]=[CH:34][C:35]([C@H:38]5[CH2:55][C@@:53]6([CH3:54])[C@@H:49]([CH2:50][CH2:51][C@:52]6([OH:59])[C:56]#[C:57][CH3:58])[C@H:48]6[C:39]5=[C:40]5[C:45]([CH2:46][CH2:47]6)=[CH:44][C:43](=[O:60])[CH2:42][CH2:41]5)=[CH:36][CH:37]=4)[CH3:31])[CH2:22][CH2:21]2)[CH2:26][C@H:2]3[O:1][CH2:64][S:65][CH3:66])[CH2:5][CH2:6]1)[CH3:15])[C:11]([OH:13])=[O:12]