HRID979387

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

HCID2796029

1H-Benzotriazol-1-ol--water (1/1)

C6H7N3O2

$结构：NC(=O)CO/N=C(\C(=O)O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1$

HCID12816813

未命名化合物

结构：CC#C/C=C/C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1.Cl

HCID131715146

未命名化合物

PRODUCTS

生成物

$结构：CC#C/C=C/C1C=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)/C(=N\OCC(N)=O)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)[C@H]2S1$

HCID178442197

未命名化合物

收率 54.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

溶剂HCID8471

Triethylamine

C6H15N

PROCEDURE

实验过程

A stirred solution of diphenylmethyl(6R,7R)-7-amino-3-[(E)-pent-1-en-3-ynyl]ceph-3-em-4-carboxylate, hydrochloride (432 mg) in tetrahydrofuran (10 ml) was treated with triethylamine (125 μl). (Z)-2-(Carbamoylmethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (441 mg), 1-hydroxybenzotriazole hydrate (162 mg) and N,N'-dicyclohexylcarbodiimide (248 mg) were added in that order. After 3 h, the precipitated N,N'-dicyclohexylurea was filtered off, the filtrate evaporated and the residue purified by column chromatography (60 g silica gel). Elution with ethyl acetate:dichloromethane (1:3) gave the title compound as a foam (441 mg); νmax (CHBr3) 3500, 3398 (NH2 +NH), 2215 (C≡C), 1786 (β-lactam), 1722 (CO2R), 1682, 1528 cm-1 (CONH); τ(CDCl3) 4.24 (CH=CH--C≡C), 5.33 (OCH2CONH2), 6.48, 6.60 (2-CH2), 8.02 (C≡CCH 3).

WORKUP

后处理

filtrationthe precipitated N,N'-dicyclohexylurea was filtered off
customthe filtrate evaporated
customthe residue purified by column chromatography (60 g silica gel)
washElution with ethyl acetate:dichloromethane (1:3)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-efb420cb9d8745abb8fb8a0d26a4243e
来源数据集: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04666899
来源说明: uspto-grants-1987_05

反应 SMILES

Cl.[NH2:2][C@@H:3]1[C:31](=[O:32])[N:5]2[C:6]([C:15]([O:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[C:7](/C=C/C#CC)[CH2:8][S:9][C@H:4]12.[C:33]([CH2:36][O:37]/[N:38]=[C:39](/[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[S:46][CH:47]=1)\[C:40]([OH:42])=O)(=[O:35])[NH2:34].O.ON1[C:74]2[CH:75]=C[CH:77]=[CH:78][C:73]=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(N(CC)CC)C>[C:33]([CH2:36][O:37]/[N:38]=[C:39](/[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[S:46][CH:47]=1)\[C:40]([NH:2][C@@H:3]1[C:31](=[O:32])[N:5]2[C:6]([C:15]([O:17][CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:16])=[CH:7][CH:8](/[CH:75]=[CH:74]/[C:73]#[C:78][CH3:77])[S:9][C@H:4]12)=[O:42])(=[O:35])[NH2:34]