Allyl chloroformate → (2R)-4-(methylsulfanyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}butanoic acid

HRID 1719467

反応式

HRID 1719467 の反応式
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].Cl[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12]>[OH-].[Na+]>[CH2:14]([O:13][C:11]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:12])[CH:15]=[CH2:16]

参加物

4

反応物 2

HCID 18052Allyl chloroformateHCID 84815D-Methionine

生成物 1

HCID 13491536(2R)-4-(methylsulfanyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}butanoic acid

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

実験手順

To a solution of 15.00 g D-methionine in 25.2 ml 4N sodium hydroxide cooled to about 0° C. is added, with stirring, 15.60 ml allyl chloroformate and 41.49 ml 4N sodium hydroxide. After the addition is completed, the reaction is stirred for an additional ten minutes at 0° C. and then allowed to warm to room temperature for an additional 20 minutes. The reaction mixture is then washed twice with ethyl ether. The aqueous layers are separated, acidified to pH2 with concentrated hydrochloric acid and then refrigerated for one hour. The cooled solution is then extracted three times with 100 ml portions of ethyl ether. The ether extracts are combined, dried over anhydrous sodium sulfate and the solvents removed under vacuum to afford the title product having

後処理

  1. additionis added
  2. additionAfter the addition
  3. stirringthe reaction is stirred for an additional ten minutes at 0° C.
  4. washThe reaction mixture is then washed twice with ethyl ether
  5. customThe aqueous layers are separated
  6. extractionThe cooled solution is then extracted three times with 100 ml portions of ethyl ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvents removed under vacuum

出典と根拠

ORDレコード
ord-74c258d437ca43748c31026d47517f4e
出典データセット
uspto-grants-1985_09
特許番号
US04540580

関連ノート

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