HRID1982312

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

结构：CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)O

HCID178451946

未命名化合物

结构：CC[C@H](C)[C@H](NC(=O)C[C@H](O)[C@@H](N)CC(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)OC

HCID178455903

未命名化合物

PRODUCTS

生成物

结构：CC[C@H](C)[C@H](NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)OC

HCID178455896

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

480 mg of Boc-Pro-His-Pro-Phe-His-OH (for manufacture see Example 1, stage 1.9), 340 mg of H-Sta-Ile-His-Lys(Boc)-OMe and 150 mg of HONB are dissolved, while heating, in 3.5 ml of DMF. After cooling to 0°, 170 mg of DCCI are added, whereupon stirring is carried out for 5 hours at 0° and the whole is left to stand at room temperature for 20 hours. The condensation product is precipitated by the addition of 35 ml of diisopropyl ether and filtered off. It is purified by Craig partitioning over 1000 stages in the same solvent system as described in stage 2.4 (K=0.6), yielding Boc-Pro-His-Pro-Phe-His-Sta-Ile-His-Lys(Boc)-OMe; Rf (A)=0.22; Rf (B)=0.21; Rf (E)=0.54.

WORKUP

后处理

temperatureAfter cooling to 0°
waitthe whole is left
waitto stand at room temperature for 20 hours
customThe condensation product is precipitated by the addition of 35 ml of diisopropyl ether
filtrationfiltered off
customIt is purified by Craig
custompartitioning over 1000 stages in the same solvent system

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f9fc76e9fd1d4c82addc793321b6312b
来源数据集: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04595677
来源说明: uspto-grants-1986_06

反应 SMILES

[N:1]1([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:46][CH2:45][CH2:44][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:43][CH2:42][CH2:41][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38](O)=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4].[NH2:54][C@H:55]([C@H:60]([CH2:62][C:63]([NH:65][C@H:66]([C:71]([NH:73][C@H:74]([C:81]([NH:83][C@H:84]([C:97]([O:99][CH3:100])=[O:98])[CH2:85][CH2:86][CH2:87][CH2:88][NH:89][C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])=[O:82])[CH2:75][C:76]1[N:80]=[CH:79][NH:78][CH:77]=1)=[O:72])[C@H:67]([CH2:69][CH3:70])[CH3:68])=[O:64])[OH:61])[CH2:56][CH:57]([CH3:59])[CH3:58].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[N:1]1([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:46][CH2:45][CH2:44][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:43][CH2:42][CH2:41][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([NH:54][C@H:55]([C@H:60]([CH2:62][C:63]([NH:65][C@H:66]([C:71]([NH:73][C@H:74]([C:81]([NH:83][C@H:84]([C:97]([O:99][CH3:100])=[O:98])[CH2:85][CH2:86][CH2:87][CH2:88][NH:89][C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])=[O:82])[CH2:75][C:76]1[N:80]=[CH:79][NH:78][CH:77]=1)=[O:72])[C@H:67]([CH2:69][CH3:70])[CH3:68])=[O:64])[OH:61])[CH2:56][CH:57]([CH3:58])[CH3:59])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4]