Sodium Bicarbonate → HCID 21454858、化合物

HRID 435967ノート

反応式

HRID 435967 の反応式
[Na].C(O[CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:25])[CH:11]2[NH:15][C:16](=[O:24])[CH2:17][C:18]2[S:19][CH2:20][CH2:21][S:22][CH:23]=2)[C:8]=1[C:26]([OH:28])=[O:27])(=O)C.C(=O)(O)[O-].[Na+].[CH3:34][C:35]1[S:36][C:37](=[S:40])[NH:38][N:39]=1>O.C(OC(C)C)(C)C>[C:26]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[CH2:6][S:40][C:37]1[S:36][C:35]([CH3:34])=[N:39][N:38]=1)[CH:11]([NH:15][C:16](=[O:24])[CH2:17][C:18]1[S:19][CH2:20][CH2:21][S:22][CH:23]=1)[C:10]2=[O:25])([OH:28])=[O:27]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 5360545SodiumHCID 21454859HCID 21454859、化合物

生成物 1

HCID 21454858HCID 21454858、化合物収率 51.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7914Diisopropyl Ether溶媒

反応条件

温度
60 °C

実験手順

The sodium salt of 3 -acetoxymethyl-2-carboxy-7-[(5,6-dihydro-1,4-dithiin-2-yl )acetamido]-8-oxo-5-thia-1-aza-bicyclo [4,2,0]oct-2-ene (10 g.) is dissolved in distilled water (200 cc.). Sodium bicarbonate (2.25 g.) followed by 2-methyl-5-thioxo-1,3,4-thiadiazoline (3.54 g.) are added to the solution and the mixture is heated with stirring at 60° C. for 16 hours. After cooling, the reaction mixture is washed with ethyl acetate (200 cc.). The pH of the mixture is brought to 6.5 by addition of 4N hydrochloric acid and then the mixture is washed again with ethyl acetate (200 cc.). The mixture is acidified to pH 2 by addition of 4N hydrochloric acid in the presence of ethyl acetate (200 cc.). After decanting the organic phase, the aqueous phase is extracted twice with ethyl acetate (total 200 cc.). The organic extracts are combined, washed three times with water (total 500 cc.), dried over sodium sulphate, treated with decolourizing charcoal, filtered and then concentrated to dryness under reduced pressure (20 mm.Hg). The solid residue obtained is taken up in diisopropyl ether (200 cc.), filtered off and then dried under reduced pressure (2 mm.Hg). 2-Carboxy-7-[(5,6-dihydro-1,4-dithiin-2-yl )acetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl )thiomethyl]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (6 g.), melting at 170° C., is thus obtained.

後処理

  1. additionare added to the solution
  2. temperaturethe mixture is heated
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with ethyl acetate (200 cc.)
  5. additionThe pH of the mixture is brought to 6.5 by addition of 4N hydrochloric acid
  6. washthe mixture is washed again with ethyl acetate (200 cc.)
  7. additionThe mixture is acidified to pH 2 by addition of 4N hydrochloric acid in the presence of ethyl acetate (200 cc.)
  8. customAfter decanting the organic phase
  9. extractionthe aqueous phase is extracted twice with ethyl acetate (total 200 cc.)
  10. washwashed three times with water (total 500 cc.)
  11. dry with materialdried over sodium sulphate
  12. additiontreated with decolourizing charcoal
  13. filtrationfiltered
  14. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  15. customThe solid residue obtained
  16. filtrationfiltered off
  17. customdried under reduced pressure (2 mm.Hg)

出典と根拠

ORDレコード
ord-f8c908e1ddc2467982ae6d20c7c474cf
出典データセット
uspto-grants-1977_02
特許番号
US04007176

反応ノート

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