HRID414000

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8082

Piperidine

C5H11N

结构：C=CCOC(=O)C[C@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)NS(=O)(=O)c1c(C)c(C)c2c(c1C)CCC(C)(C)O2)NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1

HCID178459568

Fmoc-Glu(OBut)-Arg(Pmc)-Val-Asp(Allyl)-OBzl

C63H81N7O14S

PRODUCTS

生成物

结构：C=CCOC(=O)C[C@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)NS(=O)(=O)c1c(C)c(C)c2c(c1C)CCC(C)(C)O2)NC(=O)[C@@H](N)CCC(=O)OC(C)(C)C)C(C)C)C(=O)OCc1ccccc1

HCID178459569

Glu(OtBu)-Arg(Pmc)-Val-Asp(Allyl)-OBzl

C48H71N7O12S

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8900

Heptane

C7H16

PROCEDURE

实验过程

To a solution of Fmoc-Glu(OBut)-Arg(Pmc)-Val-Asp(OAllyl)-OBzl (SEQ ID NO: 37) (12.3 g, 10.3 mmol) in 105 mL of dichloromethane is added piperidine (3.5 g, 41.3 mmol) at ambient temperature. The mixture is stirred 2 hours, then diluted with heptane, concentrated to half volume, and left standing in the freezer overnight. The liquor is decanted from the oily residue, which is then taken up in dichloromethane. The solution is washed with 0.5M aqueous citric acid, water, and brine, dried (magnesium sulfate), filtered, and concentrated. The crude solid is triturated twice with heptane and filtered to give 9.0 g of Glu(OtBu)-(L)Arg(Pmc)-Val-Asp(OAllyl)-OBzl as a white powder. (Mcalc 970.2; M+1obsvd 971).

WORKUP

后处理

concentrationconcentrated to half volume
waitleft
customstanding in the freezer overnight
customThe liquor is decanted from the oily residue, which
washThe solution is washed with 0.5M aqueous citric acid, water, and brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated
customThe crude solid is triturated twice with heptane
filtrationfiltered

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-20a68893bed0432f9a3b3628f369c0f6
来源数据集: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06569993B1
来源说明: uspto-grants-2003_05

反应 SMILES

[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:41]([NH:43][C@H:44]([C:48]([NH:50][C@H:51]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[CH2:52][C:53](=[O:58])[O:54][CH2:55][CH:56]=[CH2:57])=[O:49])[CH:45]([CH3:47])[CH3:46])=[O:42])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:40])[NH:21][S:22]([C:25]1[C:38]([CH3:39])=[C:36]([CH3:37])[C:35]2[O:34][C:31]([CH3:33])([CH3:32])[CH2:30][CH2:29][C:28]=2[C:26]=1[CH3:27])(=[O:24])=[O:23])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].N1CCCCC1>ClCCl.CCCCCCC>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:41]([NH:43][C@H:44]([C:48]([NH:50][C@H:51]([C:59]([O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:60])[CH2:52][C:53](=[O:58])[O:54][CH2:55][CH:56]=[CH2:57])=[O:49])[CH:45]([CH3:47])[CH3:46])=[O:42])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:40])[NH:21][S:22]([C:25]1[C:38]([CH3:39])=[C:36]([CH3:37])[C:35]2[O:34][C:31]([CH3:33])([CH3:32])[CH2:30][CH2:29][C:28]=2[C:26]=1[CH3:27])(=[O:23])=[O:24])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]