4-Methylmorpholine → HCID 131717475、化合物

HRID 655057

反応式

HRID 655057 の反応式
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19]C(=O)CC4C=CC=CC=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:5][CH:4]=1.CN1CCOCC1.[C:41]([O:45][C:46]([NH:48][C:49]1[S:50][CH:51]=[C:52]([C:54](=[N:58][O:59][C:60]([C:63]([O:65][CH:66]([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])([CH3:62])[CH3:61])[C:55](O)=[O:56])[N:53]=1)=[O:47])([CH3:44])([CH3:43])[CH3:42].C1C=CC(OP(Cl)(Cl)=O)=CC=1>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:55](=[O:56])[C:54]([C:52]4[N:53]=[C:49]([NH:48][C:46]([O:45][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:47])[S:50][CH:51]=4)=[N:58][O:59][C:60]([C:63]([O:65][CH:66]([C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)[C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)=[O:64])([CH3:61])[CH3:62])[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:32][CH:33]=1

参加物

7

反応物 4

HCID 79724-Methylmorpholine2 回HCID 13038Phosphorodichloridic acid, phenyl esterHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 542728292-(2-t-Butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetic acid

生成物 1

HCID 131717475HCID 131717475、化合物収率 83.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) p-toluenesulfonate (2.705 g: 5 mMol.) in dichloromethane (50 ml) are added N-methylmorpholin (0.55 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetic acid (3.51 g; 1.3 Eq.) at 0° C. and then phenylphosphoric dichloride (0.97 ml; 1.3 Eq.) and N-methylmorpholin (1.65 ml; 3 Eq.) at -40° C., and the mixture is stirred at -40° to -10° C. for 1.5 hours. The reaction mixture is diluted with ethyl acetate, washed with water, diluted hydrochloric acid and water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene:ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (3.70 g).

後処理

  1. washwashed with water, diluted hydrochloric acid and water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by silica gel chromatography (toluene:ethyl acetate)

出典と根拠

ORDレコード
ord-a3d248e291de4d8d9313a6d8c07afc6e
出典データセット
uspto-grants-1992_07
特許番号
US05134138

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