(-)-Cystine → N,N'-Bis[2-methyl-2-(methylthio)propanoyl]-L-cystine

HRID 462655

反応式

HRID 462655 の反応式
[CH2:1]([S:7][S:8][CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])[C@H:2]([NH2:6])[C:3]([OH:5])=[O:4].[CH3:15][C:16]([S:21][CH3:22])([CH3:20])[C:17](Cl)=[O:18]>[OH-].[Na+]>[CH3:15][C:16]([S:21][CH3:22])([CH3:20])[C:17]([NH:6][C@H:2]([C:3]([OH:5])=[O:4])[CH2:1][S:7][S:8][CH2:9][C@H:10]([NH:14][C:17](=[O:18])[C:16]([S:21][CH3:22])([CH3:20])[CH3:15])[C:11]([OH:13])=[O:12])=[O:18]

参加物

4

反応物 2

HCID 67678(-)-CystineHCID 134719922-Methyl-2-(methylthio)propanoyl chloride

生成物 1

HCID 13471994N,N'-Bis[2-methyl-2-(methylthio)propanoyl]-L-cystine収率 83.6%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

To a stirred solution of 3.1 g (13 mM) of L-cystine in 105 ml of 0.5 N sodium hydroxide, 4.0 g (26 mM) of 2-methyl-2-(methylthio)propanoyl chloride is added dropwise at 5°-10° C. After the addition the reaction mixture is stirred for 45 minutes at the same temperature and for additional 20 minutes at the room temperature. The reaction mixture is washed with ether, acidified with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer is washed with water and dried. Ehtyl acetate is distillated off and the residue is purified by silica gel column chromatography to give 5.1 g (83%) of the titled compound.

後処理

  1. additionAfter the addition the reaction mixture
  2. washThe reaction mixture is washed with ether
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. customthe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4c52b1ec942b42118310243abe50d3ae
出典データセット
uspto-grants-1985_05
特許番号
US04517123

関連ノート

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