HRID722989

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

2 次

结构：CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)Oc1ccc([N+](=O)[O-])cc1

HCID7017891

L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl ester

C16H21N3O7

HCID21584188

Chloroform methanol

C2H5Cl3O

结构：Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](N)C(=O)N2CCC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2Cl)C(=O)OCc2ccccc2)cc1

HCID178427560

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)OC(C)(C)C)C(=O)N2CCC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2Cl)C(=O)OCc2ccccc2)cc1

HCID178427539

未命名化合物

收率 80%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

At 0° C. the solution of 467 mg (0.51 mmol) of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12) in 20 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which he pre-cold solution of 195 mg, (0.53 mmol) of Boc-Gln-Onp in 10 ml of anhydrous tetrahydrofuran was added. The reaction mixture was stirred at room temperature for 96 h and TLC (chloroform/methanol, 9:1) indicated complete disappearance of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12). The reaction mixture was evaporated to dryness and the residue was purified on sinica gel chromatography (CHCl3/CH3OH, 10:1) to provide 450 mg (80%) of the title compound as a glassy mass. Mp 80–82° C., FAB-MS (m/e) 1111.3[M+H]+, 1132.5[M+Na]+,1010.0[M-Boc]+.

WORKUP

后处理

customAt 0° C.
additionwas added
customThe reaction mixture was evaporated to dryness
customthe residue was purified on sinica gel chromatography (CHCl3/CH3OH, 10:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6ecd985ec1604a50b227e72a4313fe6a
来源数据集: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07138491B2
来源说明: uspto-grants-2006_11

反应 SMILES

Cl.[NH2:2][C@H:3]([C:21]([N:23]1[CH2:62][CH2:61][CH2:60][C@H:24]1[C:25]([NH:27][C@H:28]([C:30]([NH:32][C@H:33]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1[Cl:45])=[O:40])=[O:31])[CH3:29])=[O:26])=[O:22])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:20])[NH:9][S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[CH3:63][C:64]([O:67][C:68]([NH:70][C@H:71]([C:77](OC1C=CC([N+]([O-])=O)=CC=1)=[O:78])[CH2:72][CH2:73][C:74]([NH2:76])=[O:75])=[O:69])([CH3:66])[CH3:65].C(Cl)(Cl)Cl.CO>O1CCCC1>[NH:70]([C:68]([O:67][C:64]([CH3:66])([CH3:65])[CH3:63])=[O:69])[C@H:71]([C:77]([NH:2][C@H:3]([C:21]([N:23]1[CH2:62][CH2:61][CH2:60][C@H:24]1[C:25]([NH:27][C@H:28]([C:30]([NH:32][C@H:33]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1[Cl:45])=[O:40])=[O:31])[CH3:29])=[O:26])=[O:22])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:20])[NH:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:17])=[CH:18][CH:19]=1)(=[O:11])=[O:12])=[O:78])[CH2:72][CH2:73][C:74](=[O:75])[NH2:76]