4-Methylmorpholine → HCID 131717474、化合物

HRID 655056

反応式

HRID 655056 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.CN1[CH2:40][CH2:39]OCC1.[C:41]([O:45][C:46]([NH:48][C:49]1[S:50][CH:51]=[C:52]([C:54](=[N:58][O:59][CH2:60][C:61](OC(C)(C)C)=O)[C:55]([OH:57])=O)[N:53]=1)=[O:47])([CH3:44])([CH3:43])[CH3:42].[CH:68]1[CH:73]=[CH:72][C:71](OP(Cl)(Cl)=O)=[CH:70][CH:69]=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:57])[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:61]4[CH:40]=[CH:39][CH:12]=[CH:11][CH:9]=4)([C:3]4[CH:33]=[CH:32][CH:6]=[CH:5][CH:4]=4)[C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)[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 53716865HCID 53716865、化合物

生成物 1

HCID 131717474HCID 131717474、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-40 °C

実験手順

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) toluene-p-sulfonic acid salt (3.94 g; (7.28 mMol.) in dichloromethane (50 ml) keeping at 0° C. are added N-methylmorpholin (0.80 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetic acid (3.80 g; 1.3 Eq.) and cooled at -40° C. To this mixture are added phenylphosphoric acid dichloride (1.41 ml; 1.3 Eq.) and N-methylmorpholin (2.41 ml; 3 Eq.), and the mixture is stirred at -40° to -15° 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 toluene: ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (5.20 g).

後処理

  1. customkeeping at 0° C.
  2. washwashed with water, diluted hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography (toluene toluene: ethyl acetate)

出典と根拠

ORDレコード
ord-871313f628f1425fba0d1c59af88520e
出典データセット
uspto-grants-1992_07
特許番号
US05134138

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