HRID358170

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)[O-])=C(COC(C)=O)CS[C@H]23)c2ccc(NC(=O)OC[C@@H](N)C(=O)O)cc2)C(=O)C1=O.[Na+]

HCID131713656

未命名化合物

HCID178483731

未命名化合物

PRODUCTS

生成物

结构：CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(C(CCN(C)C)Sc4nnn[nH]4)CS[C@H]23)c2ccc(NC(=O)OC[C@@H](N)C(=O)O)cc2)C(=O)C1=O

HCID178462780

未命名化合物

PROCEDURE

实验过程

2.3 g of 3-acetoxymethyl-7β-{(2R)-2-[4-((2R)-2-amino-2-carboxyethoxycarbonylamino)-phenyl]-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido}-3-cephem-4-carboxylic acid sodium salt and 1.16 g of 1-(2-dimethylaminoethyl)-5-mercapto-1H-tetrazole are dissolved in 12 ml of twice-distilled and degassed water. The solution is then adjusted to a pH of 6.2 with 1N aqueous NaOH and then stirred at 65° for 4 hours under a nitrogen atmosphere. It is then cooled, adjusted to a pH of 5 with 1N HCl and introduced into 600 ml of ethanol. The resulting precipitate is filtered with suction, washed with alcohol and ether and dried. The crude product is then separated over a column of 100 g of silylated silica gel (Opty-Up C 12; ANTEC AG, CH-4431 Bennwil) and 40 ml fractions are taken. Fractions 1-13 are eluted with H2O/acetonitrile (97:3), fractions 14-20 with H2O/acetonitrile (93:7), fractions 21-28 with H2O/acetonitrile (9:1) and the later fractions with H2O/acetonitrile (4:1). By concentrating by evaporation and reprecipitating from H2O/ethanol fractions 33-35, 3-[1-(2-dimethylaminoethyl)-1H-tetrazol-5-ylthiomethyl]-7β-{(2R)-2-[4-((2R)-2-amino-2-carboxyethoxycarbonylamino)-phenyl]-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido}-3-cephem-4-carboxylic acid is obtained. Decomposition from 165°. [α]D20 =+34°±1° (0.67% in H2O). IR: 3400 (shoulder), 3280 (wide), 1770, 1720, 1680, 1612, 1515 cm-1 (Nujol).

WORKUP

后处理

distillationof twice-distilled
customdegassed water
temperatureIt is then cooled
additionintroduced into 600 ml of ethanol
filtrationThe resulting precipitate is filtered with suction
washwashed with alcohol and ether
customdried
customThe crude product is then separated over a column of 100 g of silylated silica gel (Opty-Up C 12; ANTEC AG, CH-4431 Bennwil) and 40 ml fractions
washFractions 1-13 are eluted with H2O/acetonitrile (97:3), fractions 14-20 with H2O/acetonitrile (93:7), fractions 21-28 with H2O/acetonitrile (9:1)
concentrationBy concentrating by evaporation
customreprecipitating from H2O/ethanol fractions 33-35

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-030c2392c4b34caf9dc414e443d8ba1c
来源数据集: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04464366
来源说明: uspto-grants-1984_08

反应 SMILES

[Na+].C(O[CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:50])[C@@H:20]([C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41]([O:43][CH2:44][C@@H:45]([NH2:49])[C:46]([OH:48])=[O:47])=[O:42])=[CH:36][CH:35]=3)[NH:21][C:22]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[C:26](=[O:32])[C:25]3=[O:33])=[O:23])[C:16](=[O:51])[N:11]2[C:12]=1[C:13]([O-:15])=[O:14])(=O)C.CN(C)CC[N:56]1[C:60]([SH:61])=[N:59][N:58]=[N:57]1>>[CH3:12][N:11]([CH3:16])[CH2:10][CH2:17][CH:6]([S:61][C:60]1[NH:59][N:58]=[N:57][N:56]=1)[C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:50])[C@@H:20]([C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41]([O:43][CH2:44][C@@H:45]([NH2:49])[C:46]([OH:48])=[O:47])=[O:42])=[CH:36][CH:35]=3)[NH:21][C:22]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[C:26](=[O:32])[C:25]3=[O:33])=[O:23])[C:16](=[O:51])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14]