Bromochloromethane → (3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone

HRID 413988ノート

反応式

HRID 413988 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])OC1C1C=CC(OC)=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:33][Cl:34].O1CCCC1.S([O-])(O)(=O)=O.[K+]>CCCCCC>[CH2:1]([O:8][C:9]([NH:11][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:14](=[O:23])[CH2:33][Cl:34])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6333BromochloromethaneHCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 11015253(4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one

生成物 1

HCID 99625(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone収率 62%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

(4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one (Tetrahedron Lett. 1995, 36, 42, 7761) (700 mg) and bromochloromethane (0.142 ml) were added to dehydrated tetrahydrofuran (16.8 ml), and they were cooled to −78° C. 1.54 Mn-butyllithium solution (1.42 ml) in hexane was added to the obtained mixture, and they were stirred for 33 minutes. 5% aqueous potassium hydrogensulfate solution was added to the reaction mixture to terminate the reaction. After the extraction with ethyl acetate at room temperature twice followed by drying over anhydrous magnesium sulfate, magnesium sulfate was removed. The obtained solution in ethyl acetate was analyzed by HPLC to find that (3S)-3-benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone (347 mg) was obtained in a yield of 62%.

後処理

  1. customto terminate
  2. customthe reaction
  3. extractionAfter the extraction with ethyl acetate at room temperature
  4. dry with materialby drying over anhydrous magnesium sulfate, magnesium sulfate
  5. customwas removed
  6. customwas obtained in a yield of 62%

出典と根拠

ORDレコード
ord-d6730c6f6557447dbb53996b5e245712
出典データセット
uspto-grants-2003_05
特許番号
US06570039B2

反応ノート

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