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

HRID 2207140노트

반응식

HRID 2207140 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f54a3032e8504e9da62a3c65d6e4fadf
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376424B2

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