Sulfuric Acid → L-Phenylalanine, methyl ester

HRID 129245

反応式

HRID 129245 の反応式
S(=O)(=O)(O)O.[NH2:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N[C@@H:19](C(O)=O)CC1C=CC=CC=1>CO>[CH3:19][O:16][C:15](=[O:17])[C@H:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:6]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 6140L-Phenylalanine2 回HCID 71567D-Phenylalanine2 回

生成物 1

HCID 736234L-Phenylalanine, methyl ester収率 12.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

5.8 ml of 95% sulfuric acid was added to 33 ml of methanol and heat-refluxed. Subsequently, methanol was removed under reduced pressure and water was added to provide 15 ml of CH3SO4H solution. 2.7 g L-Phe and 0.3 g (D-Phe/L-Phe=11.1%) D-Phe were added thereto and dissolved by heat, following which was then cooled with ice. The separated crystals were isolated by suction filtration and washed with a small amount of cold water. Yield, 3.73 g. The results of HPLC analysis using an optically active column revealed that the crystals contained 1.66 g L-Phe and 0.049 g (D-Phe/L-Phe=2.9%) D-Phe. In addition, 41 mg of L-phenylalanine methyl ester was also produced as a result of esterification of L-Phe with the methanol remaining in the CH3SO4H solution.

後処理

  1. temperatureheat-refluxed
  2. customSubsequently, methanol was removed under reduced pressure and water
  3. additionwas added
  4. customto provide 15 ml of CH3SO4H solution
  5. dissolutiondissolved
  6. temperatureby heat
  7. temperaturewas then cooled with ice
  8. customThe separated crystals were isolated by suction filtration
  9. washwashed with a small amount of cold water
  10. customYield
  11. customThe results of HPLC analysis

出典と根拠

ORDレコード
ord-7f4b21ad64ac4f83bd865c93e0c33688
出典データセット
uspto-grants-1995_11
特許番号
US05466864

関連ノート

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