Sodium borohydride → HCID 70390815、化合物

HRID 978874ノート

反応式

HRID 978874 の反応式
[BH4-].[Na+].C[O:4][C:5]([C@H:7]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])[C:9](=[O:22])[C@H:8]1[NH:23][C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O>O1CCCC1>[CH3:21][O:20][C:13]1[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=1[CH2:11][N:10]1[C@H:7]([CH2:5][OH:4])[C@H:8]([NH:23][C:24](=[O:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:22]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 70390633HCID 70390633、化合物

生成物 1

HCID 70390815HCID 70390815、化合物収率 91.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under ice-cooling and stirring, 12 ml of an aqueous solution containing 570 mg of sodium borohydride is added to a solution of 2.06 g of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester in 24 ml of tetrahydrofuran. The reaction mixture is stirred for 30 minutes under ice-cooling and then for 1.5 hours at room termperature. The tetrahydrofuran is distilled off in vacuo and an aqueous sodium chloride solution and ethyl acetate are added to the residue. The resulting ethyl acetate layer is separated and washed successively with an aqueous sodium hydrogen carbonate and an aqueous sodium chloride. It is then dried over magnesium sulfate and the solvent is distilled off in vacuo. Ether is added to the residue and the precipitated crystals are collected by filtration to give 1.75 g (91%) of cis-1-(2,4-dimethoxybenzyl)-4-hydroxymethyl-3-phenylacetamido-2-oxoazetidine, m.p. 152°-154° C.

後処理

  1. temperatureUnder ice-cooling
  2. stirringThe reaction mixture is stirred for 30 minutes under ice-
  3. temperaturecooling
  4. distillationThe tetrahydrofuran is distilled off in vacuo
  5. additionan aqueous sodium chloride solution and ethyl acetate are added to the residue
  6. customThe resulting ethyl acetate layer is separated
  7. washwashed successively with an aqueous sodium hydrogen carbonate
  8. dry with materialIt is then dried over magnesium sulfate
  9. distillationthe solvent is distilled off in vacuo
  10. additionEther is added to the residue
  11. filtrationthe precipitated crystals are collected by filtration

出典と根拠

ORDレコード
ord-f8ba22f9c269442bb02cfb8518e63a19
出典データセット
uspto-grants-1987_05
特許番号
US04665067

反応ノート

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