HRID616485

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[C@H](N)C(=O)OCc1ccccc1.Cc1ccc(S(=O)(=O)O)cc1

HCID6451312

O-Benzyl-L-leucine toluene-p-sulphonate

C20H27NO5S

HCID131710603

未命名化合物

结构：N=C(NCCC[C@H](NC(=O)CCNC(=O)OCc1ccccc1)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O)N[N+](=O)[O-]

HCID178512168

未命名化合物

PRODUCTS

生成物

结构：CC(C)C[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](CCCNC(=N)N[N+](=O)[O-])NC(=O)CCNC(=O)OCc1ccccc1)C(=O)OCc1ccccc1

HCID178445956

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: -10 °C

PROCEDURE

实验过程

In 5 ml. of DMF was dissolved 275 mg. of H-Leu-OBzl-p-toluenesulfonate and the solution was neutralized with 0.9 ml. of 10 % N-ethylmorpholine-DMF. Under cooling at -10° C, 670 mg. of Z-β-Ala-Arg(NO2)-Gly-Phe-Phe-Tyr-OH, 251 mg. of HONB and 289 mg. of DCC were added. The mixture was stirred for 12 hours and the formed DC-urea was filtered off. The DMF was distilled off under reduced pressure and 30 ml. of water was added to the residue. The resulting precipitate was collected by filtration, washed with hot methanol and dried. Yield 703 mg. (87.9 %) melting point: 178- 181° C; α!D23 -15.0°(c=1.02 %, DMF)

WORKUP

后处理

filtrationthe formed DC-urea was filtered off
distillationThe DMF was distilled off under reduced pressure and 30 ml
additionof water was added to the residue
filtrationThe resulting precipitate was collected by filtration
washwashed with hot methanol
customdried
customα!D23 -15.0°(c=1.02 %, DMF)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9513be9ed3db40c3ad219404962f9d2e
来源数据集: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04073890
来源说明: uspto-grants-1978_02

反应 SMILES

[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].CC1C=CC(S(O)(=O)=O)=CC=1.C(N1CCOCC1)C.CN(C=O)C.[NH:41]([C:99]([O:101][CH2:102][C:103]1[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=1)=[O:100])[CH2:42][CH2:43][C:44]([NH:46][C@H:47]([C:58]([NH:60][CH2:61][C:62]([NH:64][C@H:65]([C:73]([NH:75][C@H:76]([C:84]([NH:86][C@H:87]([C:96](O)=[O:97])[CH2:88][C:89]1[CH:94]=[CH:93][C:92]([OH:95])=[CH:91][CH:90]=1)=[O:85])[CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)=[O:74])[CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:63])=[O:59])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[NH:57])[NH:53][N+:54]([O-:56])=[O:55])=[O:45].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:41]([C:99]([O:101][CH2:102][C:103]1[CH:104]=[CH:105][CH:106]=[CH:107][CH:108]=1)=[O:100])[CH2:42][CH2:43][C:44]([NH:46][C@H:47]([C:58]([NH:60][CH2:61][C:62]([NH:64][C@H:65]([C:73]([NH:75][C@H:76]([C:84]([NH:86][C@H:87]([C:96]([NH:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:97])[CH2:88][C:89]1[CH:90]=[CH:91][C:92]([OH:95])=[CH:93][CH:94]=1)=[O:85])[CH2:77][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1)=[O:74])[CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:63])=[O:59])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[NH:57])[NH:53][N+:54]([O-:56])=[O:55])=[O:45]