Ketoprofen → Dexketoprofen

HRID 1459044

反応式

HRID 1459044 の反応式
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)[C@@H](C1C=CC=CC=1)CN>CC(CC(C)=O)C>[C:1]([C:9]1[CH:10]=[C:11]([C@H:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 3825KetoprofenHCID 10176271(S)-3-Methyl-2-phenylbutylamine

生成物 1

HCID 667550Dexketoprofen収率 65.6%

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

That is, (±)-2-(3-benzoylphenyl)propionic acid (12.7 g, 50 mmol) was dissolved in MIBK (76 ml) and (S)-(+)-3-methyl-2-phenylbutylamine (4.9 g, 30 mmol) was added dropwise at 40° C. This reaction solution was stirred at 35° C. to 40° C. for one hour, followed by at room temperature for 5 hours and then at 10° C. to 15° C. for one hour. Then, the crystal precipitated was filtered, and the filter cake was washed with cold MIBK (30 ml) and dried to give a diastereomer salt (8.34 g) of (S)-(+)-2-(3-benzoylphenyl)propionic acid with (S)-(+)-3-methyl-2-phenylbutylamine. The yield of the product based on (S)-(+)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 80%. Melting point: 129°-131° C. Optical purity: 94.3% e.e.

後処理

  1. waitfollowed by at room temperature for 5 hours
  2. waitat 10° C. to 15° C. for one hour
  3. customThen, the crystal precipitated
  4. filtrationwas filtered
  5. washthe filter cake was washed with cold MIBK (30 ml)
  6. customdried

出典と根拠

ORDレコード
ord-1217c5459dd7497f9a525c87efd59867
出典データセット
uspto-grants-1998_12
特許番号
US05852209

関連ノート

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