Sodium Chloride → HCID 70579374、化合物

HRID 1974178ノート

反応式

HRID 1974178 の反応式
[O:1]=[C:2]1[NH:5][C@@H:4]([C:6](OC)=[O:7])[C@H:3]1[NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+].[H][H].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>O1CCCC1.O.C(O)(=O)C>[OH:7][CH2:6][C@H:4]1[C@@H:3]([NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2](=[O:1])[NH:5]1

参加物

9

反応物 5

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 53649703Methyl cis-3-phenoxyacetamido-4-oxoazetidine-2-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 70579374HCID 70579374、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 13.5 g (0.049 mole) of methyl cis-4-oxo-3-phenoxyacetylaminoazetidine-2-carboxylate in 975 ml of tetrahydrofuran and 100 ml of water at 0° (ice bath) was added a cold solution of 3.75 g (0.099 mole) of sodium borohydride in 250 ml of water over a period of 10 min. The solution was stirred at 0° for 40 min and then glacial acetic acid was added dropwise until hydrogen evolution ceased. Solid sodium bicarbonate and sodium chloride were added and this mixture was extracted five times with 250 ml portions of ethyl acetate. After drying the combined extracts (MgSO4), the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate, clarified with Norite and allowed to crystallize to give the title compound; tlc: ethyl acetate, silica gel GF, Rf = 0.10; mp 153°-154 ° (ethyl acetate).

後処理

  1. extractionthis mixture was extracted five times with 250 ml portions of ethyl acetate
  2. dry with materialAfter drying the combined extracts (MgSO4)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. customto crystallize

出典と根拠

ORDレコード
ord-e83b0dca19de4054af2de94d87a7d775
出典データセット
uspto-grants-1976_12
特許番号
US04000154

反応ノート

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