Triethylamine → (2R,3S)-3-azido-1-(2-fluoro-2-methylpropylamino)-4-(4-methoxyphenyl)butan-2-ol

HRID 571151노트

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HRID 571151 반응식
Cl.[F:2][C:3]([CH3:7])([CH3:6])[CH2:4][NH2:5].C(N(CC)CC)C.[N:15]([C@H:18]([C@H:28]1[CH2:30][O:29]1)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[N+:16]=[N-:17]>CC(O)C>[N:15]([C@@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[C@H:28]([OH:29])[CH2:30][NH:5][CH2:4][C:3]([F:2])([CH3:7])[CH3:6])=[N+:16]=[N-:17]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 552896302-Fluoro-2-methylpropan-1-amine hydrochlorideHCID 86700744HCID 86700744, 화합물

생성물 1

HCID 86700743(2R,3S)-3-azido-1-(2-fluoro-2-methylpropylamino)-4-(4-methoxyphenyl)butan-2-ol수율 50%

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

반응 조건

온도
60 °C

실험 절차

To a solution of 2-fluoro-2-methylpropan-1-amine-HCl (2.0 eq) and triethyl amine (4.0 eq) in iPrOH was added an iPrOH solution of (S)-2-((S)-1-azido-2-(4-methoxy-phenyl)ethyl)oxirane. The mixture was heated at 60° C. for 6 h. Upon completion the reaction mixture was concentrated then dissolved in ethyl acetate and washed with H2O. The organic layer was combined washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography. 50% yield. 1H NMR (400 MHz, Chloroform-d) δ 7.4 (d, J=8.4 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 3.80 (s, 3H), 3.64-3.57 (m, 2H), 2.96-2.88 (m, 2H), 2.78-2.68 (m, 4H), 1.42 (d, J=3.1 Hz, 3H), 1.37 (d, J=3.1 Hz, 3H).

후처리

  1. concentrationUpon completion the reaction mixture was concentrated
  2. dissolutionthen dissolved in ethyl acetate
  3. washwashed with H2O
  4. washThe organic layer was combined washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-d5086f03de514420888280191373fc09
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024038B2

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