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

HRID 1599130ノート

反応式

HRID 1599130 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 then, after returning to room temperature, ethyl acetate is added, the phases are separated by decanting, the aqueous phase is acidified with 1N aqueous hydrochloric acid solution 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, drained and dried. 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid is obtained in the form of white crystals melting at 102° C. [α]D20 =+84.6° (C=1; CHCl3)

後処理

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

出典と根拠

ORDレコード
ord-da768ae6e9dd4008bb3183c3237086dd
出典データセット
uspto-grants-1998_04
特許番号
US05739351

反応ノート

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