Citric Acid → (R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

HRID 1724720

반응식

HRID 1724720 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([O:15]C)=[O:14])[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:15])=[O:14])[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 6882203-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

생성물 1

HCID 6932185(R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid수율 47.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylate (3.0 g) is dissolved in a mixture of tetrahydrofurane (THF)/H2O (3/1; 30 ml), and LiOH.H2O (684 mg) is added. After being subjected to agitation for 3 hours at room temperature, the reaction mixture is acidified with citric acid 1N (11 ml). THF is concentrated and the aqueous phase is extracted with ethyl acetate. The organic phase is dried on MgSO4, filtered and concentrated to obtain the expected product as a viscous orange oil (1.36 g).

후처리

  1. additionis added
  2. concentrationTHF is concentrated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. customThe organic phase is dried on MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-93aca3c42f1340daaa14c8fbb1bca918
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488755B2

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