HRID638321

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID11137505

1-bromoethyl Acetate

C4H7BrO2

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

HCID13279147

未命名化合物

PRODUCTS

产物

$反应SMILES：CC(=O)OC(C)OC(=O)C1C(COC(N)=O)=CS[C@@H]2[C@H](NC(=O)/C(=N\OCC3CC3)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12$

HCID178476467

未命名化合物

收率 68.4%

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 stirred with potassium carbonate (105 mg) in N,N-dimethylformamide (5 ml) with ice water cooling under nitrogen. After five minutes, 1-acetoxy-1-ethyl bromide (300 mg) was added. After one hour at ice-bath temperature and 2.5 hours at 21°, 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 with brine, dried with magnesium sulphate and evaporated to a foam. This was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 70%) in petroleum ether (bp 40°-60°) to give the title compound (840 mg); νmax (CHBr3) 3583, 3403 (NH and NH2), 1785 (β-lactam), 1730 (ester and carbamate) and 1688 and 1513 cm-1 (amide); τ (CDCl3) includes 3.04 (NH and OCHCH3), 3.22 (thiazole proton), 4.19 and 4.70 (7-H and 6-H), 4.8 to 5.6 (3CH2 and NH2), and 5.90 (--CH2O).

WORKUP

后处理

waitAfter one hour at ice-bath temperature and 2.5 hours at 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 with brine
dry with materialdried with magnesium sulphate
customevaporated to a foam
customThis was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 70%) in petroleum ether (bp 40°-60°)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-5028e0de8b11458589144e4b78c0bd2c
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+].[C:59]([O:62][CH:63](Br)[CH3:64])(=[O:61])[CH3:60]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH:11]([C:12]([O:14][CH:63]([O:62][C:59](=[O:61])[CH3:60])[CH3:64])=[O:13])[N:10]2[C:15](=[O:52])[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@H:9]2[S:8][CH:7]=1)(=[O:3])[NH2:2]