HRID58381

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID12473

2-Pyrrolecarboxylic acid

C5H5NO2

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

HCID81531

Diisopropylethylamine

C8H19N

结构：COC(=O)[C@@H]1CCCCOc2ccc(cc2)C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N1.Cl

HCID86650244

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@@H]1CCCCOc2ccc(cc2)C[C@H](NC(=O)c2ccc[nH]2)C(=O)N[C@@H](C(C)C)C(=O)N1

HCID66846964

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Amine 47 (0.37 g) was dissolved in anhydrous DMF (5 mL). 1H-pyrrole-carboxylic acid (0.11 g), DIPEA (0.72 mL), EDC (0.25 g) and HOBt (0.2 g) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between chloroform and 1M hydrochloric acid. The aqueous phase was extracted three more times with chloroform and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 20% EtOAc/(50/70) petroleum ether to EtOAc to yield an off-white solid, 279 mg, 55%. Rf=0.15. (20% EtOAc/(50/70) petroleum ether).

WORKUP

后处理

custombefore being partitioned between chloroform and 1M hydrochloric acid
extractionThe aqueous phase was extracted three more times with chloroform
dry with materialthe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification
washeluting with a gradient of 20% EtOAc/(50/70) petroleum ether to EtOAc
customto yield an off-white solid, 279 mg, 55%

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-01ec85a685a64f97889bf9e080a77bb0
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:22][C:21](=[O:23])[C@H:20]([CH:24]([CH3:26])[CH3:25])[NH:19][C:18](=[O:27])[C@@H:17]([NH2:28])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[NH:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:36](O)=[O:37].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.C(Cl)CCl>[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20]([CH:24]([CH3:26])[CH3:25])[NH:19][C:18](=[O:27])[C@@H:17]([NH:28][C:36]([C:32]2[NH:31][CH:35]=[CH:34][CH:33]=2)=[O:37])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]