tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → tert-butyl(3S)-3-(hydroxymethyl)-4-[2-hydroxy-2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

HRID 1501926노트

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HRID 1501926 반응식
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([CH2:27][OH:28])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C(O)C>[OH:28][CH2:27][C@H:23]1[N:24]([CH2:3][CH:2]([OH:1])[C:4]2[CH:13]=[CH:12][C:7]3[C:8](=[O:11])[O:9][CH2:10][C:6]=3[CH:5]=2)[CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:22]1

참가 물질

4

반응물 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 595687155-(oxiran-2-yl)-2-benzofuran-1(3H)-one

생성물 1

HCID 71271745tert-butyl(3S)-3-(hydroxymethyl)-4-[2-hydroxy-2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
150 °C

실험 절차

5-(Oxiran-2-yl)-2-benzofuran-1(3H)-one (1.5 g, 8.5 mmol) and commercially available (S)-4-N—BOC-2-hydroxymethyl piperazine (2.394 g, 11.07 mmol) were combined in ethanol (10 mL) in a microwave tube. The mixture was degassed then heated for 60 min at 150° C. LC-MS showed the product peak. The reaction was worked up by adding ethyl acetate and washing once with brine. The organic layer was separated, dried, and concentrated to dryness. The crude product was purified by MPLC using an 80 g Redi-sep column and eluted with 50%-100% EtOAc/hexane yielding the title compound.

후처리

  1. customThe mixture was degassed
  2. additionby adding ethyl acetate
  3. washwashing once with brine
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by MPLC
  8. washeluted with 50%-100% EtOAc/hexane yielding the title compound

출처 및 근거

ORD 기록
ord-46dab300aa3e4aba998386750e6c0722
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206199B2

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