HRID839102

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID54112037

未命名化合物

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

HCID70623492

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OCC1=C(C(=O)OCOC(=O)C(N)C(C)C)N2C(=O)C(N)C2SC1

HCID53641069

未命名化合物

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

HCID54152382

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A suspension of 5 grams of 3-[(acetyloxy)methyl]-7-amino-8-amino-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, which is prepared by the general procedure described in W. German Offen. 2,236,620, are mixed in 100 ml of dimethyl formamide and stirred for 72 hours. The mixture is diluted with ethyl acetate, washed with water with aqueous bicarbonate and again with water. The organic layer is dried over magnesium sulfate, filtered, and evaporated to dryness to give 3-[(acetyloxy)methyl]-7-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 amine protecting group is removed by standard procedures to give the title product.

WORKUP

后处理

customis prepared by the general procedure
washwashed with water with aqueous bicarbonate and again with water
dry with materialThe organic layer 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-9d302a9b98c94a05bc3c9d8767b7d81e
来源数据集: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04093802
来源说明: uspto-grants-1978_06

反应 SMILES

[Na+].[C:2]([O:5][CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([CH:10](N)[CH:11]2[NH2:15])[C:8]=1[C:17]([O-:19])=[O:18])(=[O:4])[CH3:3].Cl[CH2:21][O:22][C:23](=[O:36])[C@H:24]([CH:33]([CH3:35])[CH3:34])[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].CN(C)C=[O:40]>C(OCC)(=O)C>[C:29]([O:28][C:26]([NH:25][CH:24]([CH:33]([CH3:35])[CH3:34])[C:23]([O:22][CH2:21][O:19][C:17]([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]([NH2:15])[C:10]2=[O:40])=[O:18])=[O:36])=[O:27])([CH3:32])([CH3:31])[CH3:30].[NH2:25][CH:24]([CH:33]([CH3:35])[CH3:34])[C:23]([O:22][CH2:21][O:19][C:17]([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]([NH2:15])[C:10]2=[O:40])=[O:18])=[O:36]