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Methanol → Diphenylmethyl 7beta-Amino-3-(2,5-dihydro-2-oxofuran-4-ylmethyloxy)ceph-3-em-4-carboxylate

HRID 467382
ノート
印刷プレビュー

反応式

HRID 467382 の反応式
[O:1]=[C:2]1[CH:6]=[C:5]([CH2:7][O:8][C:9]2[CH2:10][S:11][C@@H:12]3[C@H:32]([NH:33]C(=O)CC4C=CC=CC=4)[C:31](=[O:43])[N:13]3[C:14]=2[C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:4][O:3]1.CN1CCOCC1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>ClCCl.O>[NH2:33][C@@H:32]1[C:31](=[O:43])[N:13]2[C:14]([C:15]([O:17][CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[C:9]([O:8][CH2:7][C:5]3[CH2:4][O:3][C:2](=[O:1])[CH:6]=3)[CH2:10][S:11][C@H:12]12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 67908619Diphenylmethyl 3-(2,5-dihydro-2-oxofuran-4-ylmethyl oxy)-7beta-phenylacetamidoceph-3-em-4-carboxylate

生成物 1

HCID 67908486Diphenylmethyl 7beta-Amino-3-(2,5-dihydro-2-oxofuran-4-ylmethyloxy)ceph-3-em-4-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

Diphenylmethyl 3-(2,5-dihydro-2-oxofuran-4-ylmethyl oxy)-7β-phenylacetamidoceph-3-em-4-carboxylate (958 mg) was dissolved in dichloromethane (13 ml) whilst under an inert atmosphere. The solution was cooled to -20° C. before treating with N-methylmorpholine (352 μl) followed by a solution of phosphorous pentachloride in dichloromethane (12.5 ml of 40 mg ml-1 solution). After stirring for 30 min. at -20° C. the solution was treated with methanol (3.2 ml) and then allowed to warm to RT. After a further 30 min. water (4.3 ml) was added and the reaction was stirred vigorously for 60 min. Solvent was removed by evaporation in vacuo and the residue dissolved in ethyl acetate/water. The pH of the mixture was adjusted to 6.5 with 1.0M aqueous ammonia. Separation of the organic phase was followed by washing with water and brine before drying over anhydrous magnesium sulphate. Purification was accomplished by chromatography of the crude material on silica gel (Keiselgel) eluting with ethyl acetate. The title compound was finally isolated as a foam (565 mg). υmax (CH2Cl2) 1780, 1755 and 1730cm-1 ; δH(CDCl3) 3.34 (1H, d, J 17.7Hz), 3.54 (1H, d, J 17.7Hz), 4.51-4.58 (2H, m), 4.70 (2H, bs) 4.75 (1H, d, J 4.7Hz), 4.97 (1H, d, J 4.7Hz), 5.93 (1H, s), and 7.26-7.40 (10H, m). [Mass spectrum: FAB +ve ion (3NOBA/Na+) MNa+ 501].

後処理

  1. temperatureto warm to RT
  2. stirringthe reaction was stirred vigorously for 60 min
  3. customSolvent was removed by evaporation in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate/water
  5. customSeparation of the organic phase
  6. washby washing with water and brine
  7. dry with materialbefore drying over anhydrous magnesium sulphate
  8. customPurification
  9. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-db98e1379050445c8ec20cda286c1ad9
出典データセット
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05158946

反応ノート

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