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Phosphorus pentachloride → (6R,7R)-7-[[(2Z)-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]-1,2,4-thiadiazol-3-yl]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 2232438
ノート
印刷プレビュー

反応式

HRID 2232438 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11](/[C:14](=[N:18]/[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:15](O)=[O:16])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:34][C@@H:35]1[C:53](=[O:54])[N:37]2[C:38]([C:50]([OH:52])=[O:51])=[C:39]([CH2:42][O:43][C:44](=[O:49])[CH2:45][C:46](=[O:48])[CH3:47])[CH2:40][S:41][C@H:36]12>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11](/[C:14](=[N:18]/[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:15]([NH:34][C@@H:35]2[C:53](=[O:54])[N:37]3[C:38]([C:50]([OH:52])=[O:51])=[C:39]([CH2:42][O:43][C:44](=[O:49])[CH2:45][C:46](=[O:48])[CH3:47])[CH2:40][S:41][C@H:36]23)=[O:16])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24819Phosphorus pentachlorideHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 13604646(2Z)-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]-1,2,4-thiadiazol-3-yl]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetic acid

生成物 1

HCID 88417246(6R,7R)-7-[[(2Z)-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]-1,2,4-thiadiazol-3-yl]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
収率 103.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 13 g of 2-(tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2(Z)-(tert-butoxycarbonylmethoxyimino)acetic acid in 100 ml of dichloromethane, 7 g of phosphorus pentachloride is added and the mixture is stirrred for 20 minutes under ice-cooling. The reaction mixture is evaporated to dryness and to the residue is added hexane and the solvent is evaporated off again. The residue is dissolved in 5 ml of dichloromethane and the solution is added under ice-cooling to a solution prepared by allowing 10 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid and 16 g of N,O-bistrimethylsilylacetamide to react in 200 ml of dichloromethane at room temperature for one hour. The mixture is stirred at the same temperature for one hour and the solvent is then evaporated under reduced pressure. The residue is dissolved in 300 ml of ethyl acetate and the solution is washed with water and then dried over anhydrous magnesium sulfate. Then, the solvent is evaporated off and the residue is triturated with hexane. Insoluble substance is collected by filtration to give 23 g of 7β-[2-(5-tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2(Z)-(tert-butoxycarbonylmethoxyimino)acetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid.

後処理

  1. temperaturecooling
  2. customThe reaction mixture is evaporated to dryness and to the residue
  3. additionis added hexane
  4. customthe solvent is evaporated off again
  5. dissolutionThe residue is dissolved in 5 ml of dichloromethane
  6. additionthe solution is added under ice-
  7. temperaturecooling to a solution
  8. customprepared
  9. customthe solvent is then evaporated under reduced pressure
  10. dissolutionThe residue is dissolved in 300 ml of ethyl acetate
  11. washthe solution is washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThen, the solvent is evaporated off
  14. customthe residue is triturated with hexane
  15. filtrationInsoluble substance is collected by filtration

出典と根拠

ORDレコード
ord-bee01c1d3d044c1fa55bc1365d4d4ba8
出典データセット
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04788185

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート