HRID58368

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10387

Benzyl chloroformate

C8H7ClO2

HCID81531

Diisopropylethylamine

C8H19N

HCID21226138

未命名化合物

结构：COC(=O)[C@@H]1CCCCCOc2ccc(cc2)C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N1.Cl

HCID66847433

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@@H]1CCCCCOc2ccc(cc2)C[C@H](NC(=O)OCc2ccccc2)C(=O)N[C@@H](CC(C)C)C(=O)N1

HCID66847059

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

Amine 25 (0.550 g, 1.17 mmol) was dissolved in anhydrous DMF (20 mL). Benzyl chloroformate (0.250 mL, 1.76 mmol) and DIPEA (0.815 mL, 4.68 mmol) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted twice more with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc/DCM to yield an off-white solid, 0.460 g, 69%. Rf=0.32 (30% EtOAc/DCM). m.p. 91-93° C.

WORKUP

后处理

custombefore being partitioned between EtOAc and 1M hydrochloric acid
extractionThe aqueous phase was extracted twice more with EtOAc
dry with materialthe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc/DCM
customto yield an off-white solid, 0.460 g, 69%

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ba196075723b468c8a5c2fd957450f99
来源数据集: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09434762B2
来源说明: uspto-grants-2016_09

反应 SMILES

Cl.[CH3:2][O:3][C:4]([C@H:6]1[NH:23][C:22](=[O:24])[C@H:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:20][C:19](=[O:29])[C@@H:18]([NH2:30])[CH2:17][C:16]2=[CH:31][CH:32]=[C:13]([CH:14]=[CH:15]2)[O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].CCN(C(C)C)C(C)C.CCOC(C)=O.C(Cl)Cl>CN(C=O)C>[CH3:2][O:3][C:4]([C@H:6]1[NH:23][C:22](=[O:24])[C@H:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:20][C:19](=[O:29])[C@@H:18]([NH:30][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:17][C:16]2=[CH:31][CH:32]=[C:13]([CH:14]=[CH:15]2)[O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]