HRID1156948

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

HCID89529

4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-

C9H9NO3

HCID1623168

Boc-D-asparagine

C9H16N2O5

结构：CN(C(=O)CNC(=O)OCc1ccccc1)[C@@H](Cc1ccccc1)C(=O)NNC(N)=O

HCID12802621

未命名化合物

PRODUCTS

生成物

结构：CN(C(=O)CNC(=O)[C@@H](CC(N)=O)NC(=O)OC(C)(C)C)[C@@H](Cc1ccccc1)C(=O)NNC(N)=O

HCID12802629

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

2 次

PROCEDURE

实验过程

0.85 g of Z-Gly-MePhe-NHNHCONH2 is subjected to catalytic reduction in methanol, dissolved in 10 ml of DMF, and after ice-cooling, 0.46 g of BOC-(D)-Asn-OH, 0.40 g of HONB and 0.45 g of DCC are added. The mixture is stirred for 15 hours. The precipitated DCU is filtered off, the solvent is distilled off and the residue is dissolved in n-butanol. The solution is washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride in that order and dried over anhydrous sodium sulfate. The solvent is distilled off, ether is added to the residue and the mixture is filtered to obtain a powder. Yield 0.78 g; m.p. 133°-136° C.; [α]D24 -36.5° (c=1.0, DMF); Rf1 0.09.

WORKUP

后处理

temperatureafter ice-cooling
filtrationThe precipitated DCU is filtered off
distillationthe solvent is distilled off
dissolutionthe residue is dissolved in n-butanol
washThe solution is washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride in that order
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent is distilled off
additionether is added to the residue
filtrationthe mixture is filtered
customto obtain a powder

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2d066b64f30b435f9b072f8ff855f2b7
来源数据集: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04337247
来源说明: uspto-grants-1982_06

反应 SMILES

[NH:1]([C:22]([O:24]CC1C=CC=CC=1)=O)[CH2:2][C:3]([N:5]([CH3:21])[C@H:6]([C:14]([NH:16][NH:17][C:18]([NH2:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH:32]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@@H:33](C(O)=O)[CH2:34][C:35](=[O:37])[NH2:36].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CO.CN(C=O)C>[NH:32]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@@H:33]([C:22]([NH:1][CH2:2][C:3]([N:5]([CH3:21])[C@H:6]([C:14]([NH:16][NH:17][C:18]([NH2:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4])=[O:24])[CH2:34][C:35](=[O:37])[NH2:36]