HRID1448573

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID54112037

未命名化合物

结构：CC(=O)OCC1=C(C(=O)[O-])N2C(=O)C(NC(=O)Cn3cccc3C=O)C2SC1.[Na+]

HCID131711317

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OCC1=C(C(=O)OCOC(=O)C(NC(=O)OC(C)(C)C)C(C)C)N2C(=O)C(NC(=O)Cn3cccc3C=O)C2SC1

HCID86736754

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A suspension of 5 grams of 3-[(acetyloxy)methyl]-7-[[(2-formyl-1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt and 8.5 grams of N-tert-butoxycarbonyl-L-valine chloromethyl ester, prepared according to the general procedure described in W. German Offen. No. 2,236,620, are mixed in 100 ml of dimethylformamide (DMF) and stirred for 72 hours. The mixture is diluted with ethyl acetate, washed with water and aqueous sodium bicarbonate and again with water. The ethyl acetate portion is dried over magnesium sulfate, filtered and evaporated to dryness to give 3-[(acetyloxy)methyl]-7-[[(2-formyl-1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-2-amino-3-methylbutyryloxymethyl ester from which the protecting group can be removed by standard procedures to give the title compound.

WORKUP

后处理

customprepared
washwashed with water and aqueous sodium bicarbonate and again with water
dry with materialThe ethyl acetate portion is dried over magnesium sulfate
filtrationfiltered
customevaporated to dryness

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ce2ed432fb6840e4964b2ddef6e8dd87
来源数据集: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04180660
来源说明: uspto-grants-1979_12

反应 SMILES

[Na+].[C:2]([O:5][CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:26])[CH:11]2[NH:15][C:16](=[O:25])[CH2:17][N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[CH:23]=[O:24])[C:8]=1[C:27]([O-:29])=[O:28])(=[O:4])[CH3:3].Cl[CH2:31][O:32][C:33](=[O:46])[C@H:34]([CH:43]([CH3:45])[CH3:44])[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CN(C)C=O.C(OCC)(=O)C>[C:39]([O:38][C:36]([NH:35][CH:34]([CH:43]([CH3:45])[CH3:44])[C:33]([O:32][CH2:31][O:28][C:27]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[CH2:6][O:5][C:2](=[O:4])[CH3:3])[CH:11]([NH:15][C:16](=[O:25])[CH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=[O:24])[C:10]2=[O:26])=[O:29])=[O:46])=[O:37])([CH3:42])([CH3:41])[CH3:40]