Hydrochloric Acid → benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate

HRID 851383

反応式

HRID 851383 の反応式
[Si]([N:8]1[C:11](=[O:12])[CH2:10][CH:9]1[CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(C(C)(C)C)(C)C.Cl.C(=O)(O)[O-].[Na+]>CO>[O:12]=[C:11]1[NH:8][CH:9]([CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:10]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53904921benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate

生成物 1

HCID 53759236benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate収率 97.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate (45 mg) in methanol was added 1 N hydrochloric acid (0.1 ml) at 0°. After stirring at room temperature for 2.5 hours, the reaction mixture was neutrallized to pH 7 with saturated aqueous sodium bicarbonate. The resultant solution was concentrated, taken up into ethyl acetate (15 ml), and washed in turn with water and brine. Drying over magnesium sulfate and removal of the solvent left an oil, which was chromatographed on a silica gel plate (developing solvent: 6% methanol in dichloromethane) to give benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate (30 mg) as a crystalline solid.

後処理

  1. concentrationThe resultant solution was concentrated
  2. washwashed in turn with water and brine
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil, which
  5. customwas chromatographed on a silica gel plate (developing solvent: 6% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-966800ca7b2d4e40ad476f1b342a8c9c
出典データセット
uspto-grants-1983_05
特許番号
US04383945

関連ノート

読み込み中…