Hydrochloric Acid → HCID 88676167, 화합물

HRID 365225노트

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HRID 365225 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 88676167HCID 88676167, 화합물수율 63.4%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매4회

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온도
-35 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-551ef467c05e4b038e0fade54788aa43
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04608373

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