Lithium Hydroxide → 2-(4(S)-Phenyloxazolidin-2-on-3-yl)propanoic acid

HRID 2207140ノート

反応式

HRID 2207140 の反応式
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].N1CCC1=O>CO.O>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 3939Lithium HydroxideHCID 1367212-AzetidinoneHCID 66587141Methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate

生成物 1

HCID 665870702-(4(S)-Phenyloxazolidin-2-on-3-yl)propanoic acid収率 96%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate (1 g, 4.01 mmol) in 35 mL of MeOH was added, at 0° C., 14.3 mL (12.04 mmol) of a 0.84 M solution of LiOH in water. The reaction mixture was then stirred for 3 h. at ambient temperature. Upon complete hydrolysis of the azetidinone, the MeOH was removed by evaporation, the crude residue dissolved in CH2Cl2 and treated with saturated aqueous NaCl. The resulting organic layer was dried (MgSO4) and evaporated to afford the title compound (racemic mixture) as a white solid (0.906 g, 96%); 1H NMR (CDCl3) δ 1.13/1.57 (d/d, J=7.5 Hz, 3H), 3.75/4.50 (q/q, J=7.5 Hz, 1H), 4.10-4.16 (m, 1H), 4.62-4.72 (m, 1H), 4.92-5.03 (m, 1H), 7.32-7.43 (m, 5H).

後処理

  1. customthe MeOH was removed by evaporation
  2. dissolutionthe crude residue dissolved in CH2Cl2
  3. additiontreated with saturated aqueous NaCl
  4. dry with materialThe resulting organic layer was dried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-f54a3032e8504e9da62a3c65d6e4fadf
出典データセット
uspto-grants-2016_06
特許番号
US09376424B2

反応ノート

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