HRID420090

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID962

Water

H2O

HCID3939

Lithium hydroxide anhydrous

HLiO

结构：COC(=O)[C@@H]1C[C@H](Oc2cc(-c3nc(C(C)C)cs3)nc3c(Cl)c(OC)ccc23)CN1C(=O)OC(C)(C)C

HCID66650399

未命名化合物

PRODUCTS

生成物

结构：COc1ccc2c(O[C@H]3C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C3)cc(-c3nc(C(C)C)cs3)nc2c1Cl

HCID66650547

未命名化合物

收率 105.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 40 °C

PROCEDURE

实验过程

Compound 132 (20 g) was dissolved in THF (66 mL) at room temperature. Water (66 mL) was added, followed by lithium hydroxide (5 eq.) in one portion. The reaction mixture was heated at 40° C. for 3 hrs, cooled, acidified with 5M HCl, and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated under vacuum to give compound 133 (20.57 g) as a yellow form in 99% yield and 96-97% purity.

WORKUP

后处理

temperaturecooled
extractionextracted with DCM
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated under vacuum

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-58680a4eec6045f39cce9f3ce0cfa9e9
来源数据集: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08093379B2
来源说明: uspto-grants-2012_01

反应 SMILES

[Cl:1][C:2]1[C:3]([O:37][CH3:38])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:23]([C:33]([O:35]C)=[O:34])[CH2:22]1.O.[OH-].[Li+].Cl>C1COCC1>[C:29]([O:28][C:26]([N:24]1[CH2:25][C@@H:21]([O:20][C:7]2[C:6]3[C:11](=[C:2]([Cl:1])[C:3]([O:37][CH3:38])=[CH:4][CH:5]=3)[N:10]=[C:9]([C:12]3[S:13][CH:14]=[C:15]([CH:17]([CH3:18])[CH3:19])[N:16]=3)[CH:8]=2)[CH2:22][C@H:23]1[C:33]([OH:35])=[O:34])=[O:27])([CH3:30])([CH3:32])[CH3:31]