HRID1580873

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID10906

tert-Butyl nitrite

C4H9NO2

HCID2723645

Methyl histidinate--hydrogen chloride (1/2)

C7H13Cl2N3O2

结构：CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)NN

HCID131709972

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1

HCID178501421

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8471

Triethylamine

C6H15N

3 次

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

5.4 g of Z-Lys(BOC)-Phe-NH-NH2 in 40 ml of dimethylformamide are mixed at -16°C with 6.8 ml of 3.66 N HCl in dioxane and then with 1.5 ml of t-butyl nitrite. After 10 minutes at -10°C to -15°C, 3.5 ml of triethylamine are added. 3.64 g of H-His-OMe. 2 HCl are added in the solid form and 4.2 ml of triethylamine are thereafter added dropwise. The mixture is allowed to warm to 0°C over the course of 1 hour, with a pH of about 7 being set up by adding a total of 0.8 ml of triethylamine. After stirring overnight at 0°C the mixture is poured into 250 ml of water and the smeary product is obtained in the form of a powder by triturating with water. In a thin layer chromatogram on silica gel in chloroform-methanol (9:1) Rf = 0.4. Melting point 136°-137°C (from ethyl acetate).

WORKUP

后处理

additionare thereafter added dropwise
customthe smeary product is obtained in the form of a powder
customby triturating with water

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3aa2ce2b618746859272d581aaa21439
来源数据集: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US03934008
来源说明: uspto-grants-1976_01

反应 SMILES

[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28]N)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl.N(OC(C)(C)C)=O.[CH3:48][O:49][C:50]([C@@H:52](N)[CH2:53][C:54]1[NH:58][CH:57]=[N:56][CH:55]=1)=[O:51].Cl.Cl>CN(C)C=O.O1CCOCC1.O.C(N(CC)CC)C>[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:52]([C:50]([O:49][CH3:48])=[O:51])[CH2:53][C:54]1[N:58]=[CH:57][NH:56][CH:55]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]