HRID2419032

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COC(=O)C1Cc2ccccc2CN1C(=O)[C@H](CCCNC(=N)N)NS(=O)(=O)c1ccc2cc(OC)c(OC)cc2c1

HCID178496913

未命名化合物

PRODUCTS

生成物

结构：COc1cc2ccc(S(=O)(=O)N[C@@H](CCCNC(=N)N)C(=O)N3Cc4ccccc4CC3C(=O)O)cc2cc1OC

HCID178486634

未命名化合物

收率 54.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID14798

Sodium Hydroxide

HNaO

PROCEDURE

实验过程

A solution of 3 g of methyl 2-[N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate in 15 ml of methanol and 5 ml of 2N NaOH solution was warmed to 50° C and held at that temperature for 15 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 1.6 g of 2-[N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.

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-04955e7175e14413ae8c8bc1b2069d18
来源数据集: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04104392
来源说明: uspto-grants-1978_08

反应 SMILES

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH:38]([C:39]([O:41]C)=[O:40])[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]1)=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16])[CH:7]=[CH:6]2>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH:38]([C:39]([OH:41])=[O:40])[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]1)=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])(=[O:16])=[O:17])[CH:7]=[CH:6]2