Hydrochloric Acid → HCID 88676167、化合物

HRID 365225ノート

反応式

HRID 365225 の反応式
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]2[N:34]=[C:35]([NH:38][C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[S:36][CH:37]=2)/[C:27]([OH:29])=O)[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH:64]([O:77][C:78]([C:80]1[N:85]2[C:86](=[O:89])[CH:87]([NH2:88])[C@H:84]2[S:83][CH2:82][C:81]=1[CH2:90][S:91][C:92]1[N:96]([CH3:97])[N:95]=[N:94][N:93]=1)=[O:79])([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1.Cl>ClCCl.N1C=CC=CC=1>[CH:64]([O:77][C:78]([C:80]1[N:85]2[C:86](=[O:89])[CH:87]([NH:88][C:27](=[O:29])/[C:26](/[C:24]3[N:25]=[C:21]([NH:20][C:1]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[S:22][CH:23]=3)=[N:30]\[O:31][CH2:32][C:33]3[N:34]=[C:35]([NH:38][C:39]([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[S:36][CH:37]=3)[C@H:84]2[S:83][CH2:82][C:81]=1[CH2:90][S:91][C:92]1[N:96]([CH3:97])[N:95]=[N:94][N:93]=1)=[O:79])([C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 128735187-Amino-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid benzhydryl esterHCID 13578647HCID 13578647、化合物

生成物 1

HCID 88676167HCID 88676167、化合物収率 63.4%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒4 回

反応条件

温度
-35 °C

実験手順

In 6 ml of dichloromethane was suspended 500 mg of (Z)-α-(2-tritylamino-4-thiazolyl)-α-[(2-tritylamino-4-thiazolyl)methoxyimino]acetic acid and after cooling the suspension to 3°-4° C. and adding thereto 133 mg of phosphorus pentachloride, the mixture was stirred for 15 minutes at 3°-4° C. On the other hand, 316 mg of 7-amino-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid benzhydryl ester was dissolved in 6 ml of dichloromethane. After cooling the solution to -35° C. and adding 500 mg of pyridine, the foregoing dichloromethane solution containing acid chloride was added dropwise to the solution. Thereafter, the mixture was stirred for 15 minutes at -20° C. to -30° C., 20 ml of ice water was added to the reaction solution, the pH of the solution was adjusted to 1-2 with 1N hydrochloric acid, and the dichloromethane layer thus formed was separated. The dichloromethane layer was washed with water, dried (over anhydrous magnesium sulfate), and concentrated. The residue thus formed was applied to column chromatography and it was eluted with benzene and then with a mixture of benzene and ethyl acetate (5:1) to provide 510 mg of (Z)-7-{α-(2-tritylamino-4-thiazolyl)-α-[(2-tritylamino-4-thiazolyl)methoxyimino]acetamido}-3-[(1-methyl-5-tetrazolyl)thiomethyl]-3-cephem-4-carboxylic acid benzhydryl ester.

後処理

  1. temperatureafter cooling the suspension to 3°-4° C.
  2. additionadding
  3. additionwas added dropwise to the solution
  4. customwas separated
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried (over anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. customThe residue thus formed
  9. washwas eluted with benzene
  10. additionwith a mixture of benzene and ethyl acetate (5:1)

出典と根拠

ORDレコード
ord-551ef467c05e4b038e0fade54788aa43
出典データセット
uspto-grants-1986_08
特許番号
US04608373

反応ノート

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