HRID1638572

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

反应SMILES：Cc1ccc(S(=O)(=O)n2cnc(C[C@H](NC(=O)OC(C)(C)C)C(=O)O)c2)cc1

HCID6455010

Boc-His(Tos)-OH

C18H23N3O6S

反应SMILES：CC[C@H](C)[C@H](NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OC

HCID13996441

未命名化合物

PRODUCTS

产物

反应SMILES：CC[C@H](C)[C@H](NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](N)Cc1cn(S(=O)(=O)c2ccc(C)cc2)cn1)C(=O)N[C@@H](Cc1ccccc1)C(=O)OC

HCID13996501

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID176

Acetic Acid

C2H4O2

溶剂HCID21863450

未命名化合物

PROCEDURE

实验过程

Stir 0.40 g (0728 mmoles) of Boc-Sta-Ile-Phe-OCH3, as prepared in Preparation XX10II above, in 6 ml of TFA-CH2Cl2 (1:1 v/v) at room temperature for 30 minutes. Remove the solvent in vacuo and extract the residue with CH2Cl2 and aq. NaHCO3. Filter the organic layers through Na2SO4 into a flask containing 0.42 g (1.02 mmoles) of Boc-His-(Tos), concentrate the solution to a volume of about 25 ml, and add 0.21 g (1.02 mmoles) of DCC. Stir for 40 minutes, then add 1 drop of HOAc and filter off DCU. Extract the filtrate with aq. NaHCO3, filter the organic layers through Na2SO4, and remove the solvent in vacuo. The crude product is applied to a silica gel chromatography column and the product is eluted with 4% MeOH-96% CH2Cl2 to give 0.566 g (93%) of Box-His(Tos)-Sta-Ile-Phe-OCH3.

WORKUP

后处理

customRemove the solvent in vacuo
extractionextract the residue with CH2Cl2 and aq. NaHCO3
filtrationFilter the organic layers through Na2SO4 into a flask
concentrationconcentrate the solution to a volume of about 25 ml
filtrationfilter off DCU
extractionExtract the filtrate with aq. NaHCO3
filtrationfilter the organic layers through Na2SO4
customremove the solvent in vacuo
washthe product is eluted with 4% MeOH-96% CH2Cl2

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-ec5eb90055ee4c30b25f72888c68a905
来源数据集: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US04880781
来源说明: uspto-grants-1989_11

反应SMILES

[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:29]([O:31][CH3:32])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([N:50]2[CH:54]=[N:53][C:52]([CH2:55][C@H:56]([NH:60]C(OC(C)(C)C)=O)[C:57]([OH:59])=O)=[CH:51]2)(=[O:49])=[O:48])=[CH:43][CH:42]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(O)(C(F)(F)F)=O.C(Cl)Cl.CC(O)=O>[NH2:60][C@H:56]([C:57]([NH:1][C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:29]([O:31][CH3:32])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6])=[O:59])[CH2:55][C:52]1[N:53]=[CH:54][N:50]([S:47]([C:44]2[CH:43]=[CH:42][C:41]([CH3:40])=[CH:46][CH:45]=2)(=[O:48])=[O:49])[CH:51]=1