HRID529431

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6395

Methanesulfonic acid

CH4O3S

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CCN(Cc1ccccc1)C(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C

HCID110677859

未命名化合物

结构：Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)OC(C)(C)C)C(=O)O)cc1

HCID178427599

未命名化合物

PRODUCTS

生成物

结构：CCN(Cc1ccccc1)C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)NS(=O)(=O)c1ccc(C)cc1)NC(=O)OC(C)(C)C

HCID178463685

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID7964

Chlorobenzene

C6H5Cl

PROCEDURE

实验过程

Boc-Arg(Ts)-Pro-NEtBn was prepared by a similar procedure to Example 1 from Boc-Pro-NEtBn and Boc-Arg(Ts). To the solution composed of the compound (1.00 g), chlorobenzene (5.8 ml) and DBF (1.5 ml), methanesulfonic acid (1.41 g, 9.8 equivalents) was added at room temperature, and the resulting mixture was stirred at room temperature for 24 hours, thereby the Boc group was removed (reaction conversion ratio: 100.0%). After the reaction, 10% aqueous sodium carbonate solution (12 ml) was added thereto, and the resulting mixture was stirred for 15 minutes for neutralization. Then, the aqueous layer was separated off, thereby a solution containing Arg(Ts)-Pro-NEtBn (8.58 g) was obtained.

WORKUP

后处理

additionwas added at room temperature
customthe Boc group was removed
custom(reaction conversion ratio: 100.0%)
additionwas added
stirringthe resulting mixture was stirred for 15 minutes for neutralization
customThen, the aqueous layer was separated off
additiona solution containing Arg(Ts)-Pro-NEtBn (8.58 g)
customwas obtained

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-18bad930b030448ab38298c2d737e1d2
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09346850B2
来源说明: uspto-grants-2016_05

反应 SMILES

[N:1]1([C:18]([O:20]C(C)(C)C)=O)[CH2:17][CH2:16][CH2:15][C@H:2]1[C:3]([N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][CH3:7])=[O:4].[NH:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:26](C(O)=O)[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:43])[NH:32][S:33]([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(=[O:35])=[O:34].CS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[NH:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:26]([C:18]([N:1]1[CH2:17][CH2:16][CH2:15][C@H:2]1[C:3]([N:5]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:6][CH3:7])=[O:4])=[O:20])[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:43])[NH:32][S:33]([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(=[O:35])=[O:34]