Dicyclohexylcarbodiimide → Benzhydryl 7-[2-trityloxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylate

HRID 1682445ノート

反応式

HRID 1682445 の反応式
[NH2:1][CH:2]1[C:34](=[O:35])[N:4]2[C:5]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:6]([CH:9]=[CH:10][S:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH2:7][S:8][C@H:3]12.[C:36]([O:55]/[N:56]=[C:57](/[C:61]1[N:62]=[C:63]([NH:66][C:67]([C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[S:64][CH:65]=1)\[C:58](O)=[O:59])([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C=O>[C:36]([O:55][N:56]=[C:57]([C:61]1[N:62]=[C:63]([NH:66][C:67]([C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)([C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=2)[C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)[S:64][CH:65]=1)[C:58]([NH:1][CH:2]1[C:34](=[O:35])[N:4]2[C:5]([C:18]([O:20][CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:19])=[C:6]([CH:9]=[CH:10][S:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH2:7][S:8][C@H:3]12)=[O:59])([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 10327150(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic AcidHCID 131720029Benzhydryl 7-amino-3-[2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylate

生成物 1

HCID 131720028Benzhydryl 7-[2-trityloxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of benzhydryl 7-amino-3-[2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylate (a mixture of cis- and trans-isomers) (1.0 g) in a mixture of methylene chloride (10 ml) and dimethylformamide (1.0 ml) were added (Z)-2-trityloxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (1.46 g) and DCC (dicyclohexylcarbodiimide) (450 mg) and the resultant mixture was stirred at room temperature for 2 hours. After completion of the reaction, the dicyclohexylurea was filtered off and the filtrate was diluted with ethyl acetate (50 ml), washed with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure to give a crude product (2.65 g). This crude product was chromatographed on a column of silica gel and eluted with benzene-ethyl acetate to provide benzhydryl 7-[2-trityloxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylate (1.6 g).

後処理

  1. customAfter completion of the reaction
  2. filtrationthe dicyclohexylurea was filtered off
  3. additionthe filtrate was diluted with ethyl acetate (50 ml)
  4. washwashed with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customto give a crude product (2.65 g)
  8. customThis crude product was chromatographed on a column of silica gel
  9. washeluted with benzene-ethyl acetate

出典と根拠

ORDレコード
ord-d151a1217ced45548d2cdbd4e772ee99
出典データセット
uspto-grants-1997_06
特許番号
US05635500

反応ノート

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