Lithium Hydroxide → (S)-2-(2-Methoxyphenyl)propanoic acid

HRID 375422ノート

反応式

HRID 375422 の反応式
[OH-].[Li+].C[C@H]1[C@H](C2C=CC=CC=2)OC(=O)N1[C:16](=[O:27])[C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[CH3:18].C(OCC)(=[O:30])C>O1CCCC1.O>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C@H:17]([CH3:18])[C:16]([OH:27])=[O:30]

参加物

6

反応物 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 54310187(4S,5S)-4-methyl5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]2-oxazolidinone

生成物 1

HCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1.52 g of lithium hydroxide are added to a solution, cooled to +5° C., of 4.1 g of (4S,5S)-4-methyl-5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]-oxazolidin-2-one in 60 cm3 of tetrahydrofuran and 30 cm3 of water. The reaction mixture is stirred at this temperature for 3 hours and, after returning to room temperature, ethyl acetate is subsequently added, the mixture is decanted, the aqueous phase is acidified with an aqueous 1N solution of hydrochloric acid and extracted with ethyl acetate and the organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is recrystallized from hexane, filtered off and dried. 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid is obtained in the form of white crystals which melt at 102° C. [α]D20 =+84.6° (c=1; CHCl3).

後処理

  1. customafter returning to room temperature
  2. customthe mixture is decanted
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe solid obtained
  7. customis recrystallized from hexane
  8. filtrationfiltered off
  9. customdried

出典と根拠

ORDレコード
ord-713f448867fd4ad69d65f77a5424c924
出典データセット
uspto-grants-1996_01
特許番号
US05484804

反応ノート

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