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

HRID 1724720

反応式

HRID 1724720 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-93aca3c42f1340daaa14c8fbb1bca918
出典データセット
uspto-grants-2009_02
特許番号
US07488755B2

関連ノート

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