Acetic Acid → 3-Boc-amino-4-fluorobutanoic acid

HRID 354548

반응식

HRID 354548 반응식
[F:1][CH2:2][CH:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])CC=C.[Mn]([O-])(=O)(=O)=O.[K+].[C:21]([OH:24])(=[O:23])[CH3:22]>O>[F:1][CH2:2][CH:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:22][C:21]([OH:24])=[O:23]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 20508337N-Boc-1-fluoropent-4-EN-2-amine

생성물 1

HCID 205083403-Boc-amino-4-fluorobutanoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

1-Fluoro-2-tert-butoxycarbonylamino-4-pentene (1.02 g, 5 mmoles), dissolved in glacial acetic acid (15 ml), is added to potassium permanganate (2.37 g, 15 mmoles) in water (75 ml), and kept overnight at room temperature. After destroying the excess of permanganate with 10% sodium bisulfite solution and saturating with sodium chloride, the mixture is extracted twice with ether. Evaporation gives 4-fluoro-3-tert-butoxycarbonylamino-1-butanoic acid (776 mg) as a white solid which on recrystallization from ether/petroleum ether affords 676 mg (61%) of pure material, m.p. 112°-112.5° C.

후처리

  1. customAfter destroying the excess of permanganate with 10% sodium bisulfite solution
  2. concentrationsaturating with sodium chloride
  3. extractionthe mixture is extracted twice with ether
  4. customEvaporation

출처 및 근거

ORD 기록
ord-2e148432ad554c87b2a391b53bd66daf
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04375477

연결된 노트

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