HRID638323

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID3021550

1-Bromoethyl ethyl carbonate

C5H9BrO3

$反应SMILES：NC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\OCC3CC3)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)[C@H]2SC1$

HCID13279147

未命名化合物

PRODUCTS

产物

$反应SMILES：CCOC(=O)OC(C)OC(=O)C1=C(COC(N)=O)CS[C@@H]2[C@H](NC(=O)/C(=N\OCC3CC3)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12$

HCID178473645

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

Dimethylformamide

C3H7NO

PROCEDURE

实验过程

(6R,7R)-3-Carbamoyloxymethyl-7-[(Z)-2-cyclopropylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylic acid (1.1 g) was dissolved in N,N-dimethylformamide (5 ml) and stirred with potassium carbonate (105 mg) under nitrogen with ice-water cooling. After 10 minutes, 1-ethoxycarbonyloxy-1-ethyl bromide was added. After one hour, the mixtured was allowed to attain 21° and was stirred thus for three hours. The mixture was partitioned between ethyl acetate and aqueous hydrochloric acid. The aqueous layer was extracted with more ethyl acetate and the combined organic layers were washed twice with brine, dried with magnesium sulphate and concentrated. The residue was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 60%) in petroleum ether (bp 40° to 60°) to give the title compound (930 mg); [α]D21 +44.0° (c 1.30, CHCl3); λmax (ethanol) 230 nm (E1 cm1% 312), λ infl 236 nm (ED1% 295) and λnm (E1 cm1% 226).

WORKUP

后处理

waitAfter one hour
customto attain 21°
customThe mixture was partitioned between ethyl acetate and aqueous hydrochloric acid
extractionThe aqueous layer was extracted with more ethyl acetate
washthe combined organic layers were washed twice with brine
dry with materialdried with magnesium sulphate
concentrationconcentrated
customThe residue was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 60%) in petroleum ether (bp 40° to 60°)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-338e246b3ff74475b96d254311a256fd
来源数据集: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US04560683
来源说明: uspto-grants-1985_12

反应SMILES

[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:51])/[C:19](=[N:45]\[O:46][CH2:47][CH:48]3[CH2:50][CH2:49]3)/[C:20]3[N:21]=[C:22]([NH:25][C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[S:23][CH:24]=3)[C:15](=[O:52])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2].C(=O)([O-])[O-].[K+].[K+].[CH2:59]([O:61][C:62]([O:64][CH:65](Br)[CH3:66])=[O:63])[CH3:60]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:51])/[C:19](=[N:45]\[O:46][CH2:47][CH:48]3[CH2:50][CH2:49]3)/[C:20]3[N:21]=[C:22]([NH:25][C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[S:23][CH:24]=3)[C:15](=[O:52])[N:10]2[C:11]=1[C:12]([O:14][CH:59]([O:61][C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH3:60])=[O:13])(=[O:3])[NH2:2]