Hydrochloric Acid → 2-(2,3,4-Trifluoroanilino)propionic acid

HRID 8454

반응식

HRID 8454 반응식
CC(C)([O-])C.[K+].[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[CH:17][C:9]=1[NH:10][C@H:11]([CH3:16])[C:12]([O:14]C)=[O:13].[OH-].[Na+].Cl>CC(N(C)C)=O>[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[CH:17][C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([OH:14])=[O:13]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10149157Methyl (2R)-2-(2,3,4-trifluoroanilino)propionateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acid수율 98.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

Potassium tertiary-butoxide (123.4 mg) was suspended in DMAc (2 ml). Under ice-cooling, a solution of methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (223 mg, 91% ee) in DMAc (2 ml) was added thereto. The liquid reaction mixture was stirred at the same temperature for 1 hour. Then an aqueous solution of sodium hydroxide (3 mol/l; 2 ml) was added and the mixture was stirred for 1 hour. The liquid reaction mixture was adjusted to pH 2 with an aqueous solution of hydrochloric acid (3 mol/l) and then extracted with IPE. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The crude product thus obtained was recrystallized from a solvent mixture of methylene chloride with normal hexane to thereby give the title compound (206 mg) as colorless crystals. The optical purity of this product was 0% ee. Various spectral data of this product was identical with those obtained in Example 23.

후처리

  1. temperatureUnder ice-cooling
  2. customThe liquid reaction mixture
  3. stirringthe mixture was stirred for 1 hour
  4. customThe liquid reaction mixture
  5. extractionextracted with IPE
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe crude product thus obtained
  9. customwas recrystallized from a solvent mixture of methylene chloride with normal hexane

출처 및 근거

ORD 기록
ord-61b34c6c1be54403acdd2d511f0f11ed
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087778B2

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