HRID66316

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：CCOC(=O)C1CC(C)CCN1C(=O)[C@H](CCCNC(=N)N)NS(=O)(=O)c1ccc2c(c1)Sc1ccccc1O2

HCID178468857

未命名化合物

PRODUCTS

生成物

结构：CC1CCN(C(=O)[C@H](CCCNC(=N)N)NS(=O)(=O)c2ccc3c(c2)Sc2ccccc2O3)C(C(=O)O)C1

HCID178428661

未命名化合物

收率 30%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A solution of 3.5 g of ethyl 1-[N2 -(2-phenoxathiinylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate in 15 ml of methanol and 10 ml of 2N-NaOH solution was warmed to 30° C and held at that temperature for 10 hours. At the end of this period, the reaction mixture was concentrated and chromatographed on 200 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited) packed in water, washed with ethanol-water (1:4) and eluted with ethanol-water-NH4OH (10:9:1). The main fraction was evaporated to dryness and washed with ether to give 1.0 g of 1-[N2 -(2-phenoxathiinylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid as an amorphous solid. I.R. (KBr): 3400, 1625, 1460, 1165 cm-1.

WORKUP

后处理

concentrationAt the end of this period, the reaction mixture was concentrated
customchromatographed on 200 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited)
washwashed with ethanol-water (1:4)
washeluted with ethanol-water-NH4OH (10:9:1)
customThe main fraction was evaporated to dryness
washwashed with ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-047aab704e73436a836d2191650e5c2e
来源数据集: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04131673
来源说明: uspto-grants-1978_12

反应 SMILES

[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH:30]1[C:36]([O:38]CC)=[O:37])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16].[OH-].[Na+]>CO>[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH:30]1[C:36]([OH:38])=[O:37])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])(=[O:16])=[O:17]