Sodium hydride → (S)-tert-Butyl 1-cyclopropyl-3-(2-methoxyethoxy)propan-2-ylcarbamate

HRID 927595노트

반응식

HRID 927595 반응식
[H-].[Na+].[CH:3]1([CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][OH:9])[CH2:5][CH2:4]1.Br[CH2:19][CH2:20][O:21][CH3:22]>C1COCC1>[CH:3]1([CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:8][O:9][CH2:19][CH2:20][O:21][CH3:22])[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 59227079(S)-tert-Butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate

생성물 1

HCID 71105632(S)-tert-Butyl 1-cyclopropyl-3-(2-methoxyethoxy)propan-2-ylcarbamate수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

NaH (70%, 0.504 g, 15 mmol) was added in portions to a solution of (S)-tert-butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate (1.6 g, 7.5 mmol) in THF (30 mL) at room temperature. The mixture was stirred at room temperature for 20 min. 1-Bromo-2-methoxyethane (2.07 g, 15 mmol) was added and stirring was continued for 2 h. The reaction was quenched by careful addition of H2O (5 mL). After evaporation of solvent the residue was diluted with ethyl acetate (20 mL) and H2O (20 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated to give the title product as yellow oil (1.01 g, 50%); MS (EI): m/e=296.2 [M+Na]+.

후처리

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe reaction was quenched by careful addition of H2O (5 mL)
  4. customAfter evaporation of solvent the residue
  5. additionwas diluted with ethyl acetate (20 mL) and H2O (20 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d3ed993bb1434ed982dd1da157da0952
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290451B2

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