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Benzyl chloroformate → HCID 60204906、化合物

HRID 1245034
ノート
印刷プレビュー

反応式

HRID 1245034 の反応式
C(=O)([O-])O.[Na+].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[CH3:17][O:18][C:19](=[O:26])[C@@H:20]1[CH2:24][CH:23]([CH3:25])[CH2:22][NH:21]1>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19](=[O:26])[C@@H:20]1[CH2:24][CH:23]([CH3:25])[CH2:22][N:21]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 45089984HCID 45089984、化合物

生成物 1

HCID 60204906HCID 60204906、化合物収率 99%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

20 ml of an aqueous solution containing 1.89 g (22.5 mmol) of sodium hydrogencarbonate and 1.54 ml (10.8 mmol) of benzyl chloroformate were added to a solution of 0.93 g (6.5 mmol) of (2S)-4-methylproline methyl ester [obtained as described in Preparative Example 8(ii)′ above] in 20 ml of toluene, and the resulting mixture was stirred at room temperature over night. At the end of this time, the reaction mixture was extracted with ethyl acetate. The organic extract was washed with water and concentrated under reduced pressure to afford 1.78 g (yield: 99%) of (2S)-1-benzyloxycarbonyl-4-methylproline methyl ester as a pale yellow oil. Subsequently, all of the compound thus obtained was reduced using lithium borohydride, in a similar manner to that described in Preparative Example 5(i)′ above, to afford 1.07 g (yield: 66%) of the title compound as a pale yellow oil.

後処理

  1. customobtained
  2. extractionAt the end of this time, the reaction mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a546b5f1ac6d4bee8327040ac9a6e78f
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07122666B2

反応ノート

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