Ethyl (3R)-2-azido-4,4,4-trifluoro-3-methylbutanoate → Ethyl (3R)-4,4,4-trifluorovalinate

HRID 626421노트

반응식

HRID 626421 반응식
[N:1]([CH:4]([C@@H:10]([CH3:15])[C:11]([F:14])([F:13])[F:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[F:12][C:11]([F:13])([F:14])[C@H:10]([CH3:15])[C@@H:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:1]

참가 물질

5

반응물 2

HCID 90014731Ethyl (3R)-2-azido-4,4,4-trifluoro-3-methylbutanoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 124507558Ethyl (3R)-4,4,4-trifluorovalinate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

32.8 g of crude ethyl (3R)-2-azido-4,4,4-trifluoro-3-methylbutanoate (diastereomer mixture) were dissolved in 110 ml of ethanol and, after inertizing with argon, 6.98 g of palladium on carbon (5%) were added. The mixture was stirred overnight at standard pressure under an atmosphere of hydrogen, with the reaction vessel repeatedly being vented and filled with fresh hydrogen. The reaction mixture was then filtered off through Celite, the filter residue was washed with 50 ml of ethanol and the filtrate was concentrated under reduced pressure (up to about 20 mmHg). The slightly yellowish liquid that remained was briefly freed from residual solvent under high vacuum. This gave 23.5 g of the target compound as an about 70% pure crude product which was not purified any further (yield over three steps about 38% of theory).

후처리

  1. additionwere added
  2. filtrationThe reaction mixture was then filtered off through Celite
  3. washthe filter residue was washed with 50 ml of ethanol
  4. concentrationthe filtrate was concentrated under reduced pressure (up to about 20 mmHg)
  5. customThis gave 23.5 g of the target compound as an about 70% pure crude product which was not purified
  6. customany further (yield over three steps about 38% of theory)

출처 및 근거

ORD 기록
ord-d45ecd8194224e82839b9bf3de7bea70
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309198B2

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