HRID2052465

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID33032

L-Glutamic acid

C5H9NO4

结构：CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F

HCID151348

Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

C12H22F6N6OP2

结构：CC(C)CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)O)C(C)C)C(C)C

HCID5478883

Pepstatin

C34H63N5O9

PRODUCTS

生成物

结构：CC(C)CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)O)C(C)C)C(C)C.N[C@@H](CCC(=O)O)C(=O)O

HCID86736802

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID679

Dimethyl sulfoxide

C2H6OS

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8471

Triethylamine

C6H15N

PROCEDURE

实验过程

Into 8 cm3 of a mixture of dimethylformamide and dimethylsulfoxide (3-1 by volume), 130 mg of pepstatin and 120 mg of the hydrochloride of tertiobutyl diester of glutamic acid are added. Then 180 mg of BOP and 45 mg of triethylamine are added. After 72 hours of stirring, 15 cm3 of distilled water are added. The precipitate is drained and washed with 15 cm3 of ethyl ether. The product is redissolved in 30 cm3 of methanol. The insoluble residue is separated by filtration and the filtrate is evaporated. Then 10 cm3 of a mixture of methylene chloride-trifluoroacetic acid (1:1 by volume) are added, then it is allowed to stand for 30 minutes at a temperature close to 20° C. The mixture is concentrated almost to dryness. Ether is then added. The precipitate formed is separated by filtration and then washed with ether. After drying, 130 mg of pepstatin-glutamic acid are obtained whose characteristics are as follows:

WORKUP

后处理

washwashed with 15 cm3 of ethyl ether
dissolutionThe product is redissolved in 30 cm3 of methanol
customThe insoluble residue is separated by filtration
customthe filtrate is evaporated
additionThen 10 cm3 of a mixture of methylene chloride-trifluoroacetic acid (1:1 by volume) are added
waitto stand for 30 minutes at a temperature
customclose to 20° C
concentrationThe mixture is concentrated almost to dryness
additionEther is then added
customThe precipitate formed
customis separated by filtration
washwashed with ether
customAfter drying

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-332933489e444da8931f5f60169388c7
来源数据集: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04185096
来源说明: uspto-grants-1980_01

反应 SMILES

[CH3:1][C@H:2]([NH:17][C:18]([CH2:20][C@H:21]([OH:48])[C@@H:22]([NH:27][C:28]([C@@H:30]([NH:34][C:35]([C@@H:37]([NH:41][C:42]([CH2:44][CH:45]([CH3:47])[CH3:46])=[O:43])[CH:38]([CH3:40])[CH3:39])=[O:36])[CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:19])[C:3]([NH:5][C@H:6]([C@@H:11]([OH:16])[CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].Cl.[NH2:50][C@H:51]([C:57]([OH:59])=[O:58])[CH2:52][CH2:53][C:54]([OH:56])=[O:55].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O.C(N(CC)CC)C.CS(C)=O.CN(C)C=O>[CH3:1][C@H:2]([NH:17][C:18]([CH2:20][C@H:21]([OH:48])[C@@H:22]([NH:27][C:28]([C@@H:30]([NH:34][C:35]([C@@H:37]([NH:41][C:42]([CH2:44][CH:45]([CH3:47])[CH3:46])=[O:43])[CH:38]([CH3:40])[CH3:39])=[O:36])[CH:31]([CH3:32])[CH3:33])=[O:29])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:19])[C:3]([NH:5][C@H:6]([C@@H:11]([OH:16])[CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH:8]([CH3:9])[CH3:10])=[O:4].[NH2:50][C@H:51]([C:57]([OH:59])=[O:58])[CH2:52][CH2:53][C:54]([OH:56])=[O:55]