HRID1982304

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：COC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)C[C@H](O)[C@@H](N)CC(C)C)C(C)C

HCID131714719

未命名化合物

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

PRODUCTS

生成物

结构：COC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[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(C)C

HCID178501441

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

840 mg of Boc-Pro-His-Pro-Phe-His-OH, 600 mg of H-Sta-Val-Tyr-Lys(Boc)-OMe (from stage 1.5) and 250 mg of HONB are dissolved in 6 ml of DMF, cooled to 0°, and 290 mg of DCCI are added. The whole is stirred for 6 hours at 0° and for 24 hours at 25° the DCH is filtered off, and the filtrate is concentrated to dryness by evaporation. The residue is dissolved in 18.8 ml of MeOH, 0.6 ml of glacial acetic acid and 0.6 ml of H2O, heated for 1 hour at 60°, concentrated to approximately 3 ml, and the peptide is precipitated in the form of greasy material with 20 ml of diisopropyl ether. It is purified by Craig partitioning in the system MeOH/0.1N AcOH/ethylene chloride/chloroform (10:3:8:4) over 750 stages; K=0.75. The chromatographically pure middle fraction is isolated by strong concentration and lyophilisation, yielding Boc-Pro-His-Pro-Phe-His-Sta-Val-Tyr-Lys(Boc)-OMe in the form of an amorphous powder; Rfn (B)=0.38; Rf (I)=0.46; Rf (C)=0.64.

WORKUP

后处理

temperaturecooled to 0°
filtrationis filtered off
concentrationthe filtrate is concentrated to dryness by evaporation
dissolutionThe residue is dissolved in 18.8 ml of MeOH
temperature0.6 ml of glacial acetic acid and 0.6 ml of H2O, heated for 1 hour at 60°
concentrationconcentrated to approximately 3 ml
customthe peptide is precipitated in the form of greasy material with 20 ml of diisopropyl ether
customIt is purified by Craig
custompartitioning in the system MeOH/0.1N AcOH/ethylene chloride/chloroform (10:3:8:4) over 750 stages
customThe chromatographically pure middle fraction is isolated by strong concentration and lyophilisation

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e34a3c433e7b47e0b1e4ebd1dab1fb04
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:70]([NH:72][C@H:73]([C:82]([NH:84][C@H:85]([C:98]([O:100][CH3:101])=[O:99])[CH2:86][CH2:87][CH2:88][CH2:89][NH:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])=[O:83])[CH2:74][C:75]1[CH:80]=[CH:79][C:78]([OH:81])=[CH:77][CH:76]=1)=[O:71])[CH:67]([CH3:69])[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:70]([NH:72][C@H:73]([C:82]([NH:84][C@H:85]([C:98]([O:100][CH3:101])=[O:99])[CH2:86][CH2:87][CH2:88][CH2:89][NH:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])=[O:83])[CH2:74][C:75]1[CH:80]=[CH:79][C:78]([OH:81])=[CH:77][CH:76]=1)=[O:71])[CH:67]([CH3:68])[CH3:69])=[O:64])[OH:61])[CH2:56][CH:57]([CH3:59])[CH3:58])=[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]