Sulfuric Acid → L-Phenylalanine, methyl ester

HRID 129245

반응식

HRID 129245 반응식
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]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 6140L-Phenylalanine2회HCID 71567D-Phenylalanine2회

생성물 1

HCID 736234L-Phenylalanine, methyl ester수율 12.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f4b21ad64ac4f83bd865c93e0c33688
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466864

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