Citric Acid → Tert-Butyl 2-amino-3-[4-(trifluoromethoxy)phenyl]propanoate

HRID 1799294ノート

反応式

HRID 1799294 の反応式
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C1(C(=[N:27][CH:28]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][C:44]([F:47])([F:46])[F:45])=[CH:39][CH:38]=2)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:27][CH:28]([CH2:36][C:37]1[CH:38]=[CH:39][C:40]([O:43][C:44]([F:45])([F:46])[F:47])=[CH:41][CH:42]=1)[C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30]

参加物

4

反応物 2

HCID 311Citric AcidHCID 86636533Tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate

生成物 1

HCID 57972097Tert-Butyl 2-amino-3-[4-(trifluoromethoxy)phenyl]propanoate収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

According to the method described in the document (J. Am. Chem. Soc., (2003), 125, 5139-5151), a 1 M citric acid aqueous solution (52 mL) was added to a THF (52 mL) solution of tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate (2.44 g, 5.21 mmol) prepared in Reference Example 1 (1a). The mixture was stirred at room temperature for 4 hours. The reaction solution (mainly THF) was evaporated, neutralized with a sodium bicarbonate aqueous solution, and then extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 94:6, 3:7, and 1:9, V/V) to give 1.5 g of the title compound (colorless oil, yield: 95%).

後処理

  1. customThe reaction solution (mainly THF) was evaporated
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 94:6, 3:7, and 1:9, V/V)

出典と根拠

ORDレコード
ord-3eb821511f21487ca85c87963aef49ba
出典データセット
uspto-grants-2013_01
特許番号
US08344029B2

反応ノート

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