Sodium hydride → methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate

HRID 1466535

반응식

HRID 1466535 반응식
[OH:1][C@H:2]([CH:18]([CH3:20])[CH3:19])[C:3]([NH:5][C@H:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)[CH3:7])=[O:4].CS(O[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=O)=O.[H-].[Na+]>C1COCC1>[CH3:19][CH:18]([CH3:20])[C@@H:2]([O:1][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:3]([NH:5][C@H:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)[CH3:7])=[O:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2264992-Phenoxyethyl methanesulfonateHCID 86730613methyl 4-[(1S)-1-[[(2R)-2-hydroxy-3-methyl-butanoyl]amino]ethyl]benzoate

생성물 1

HCID 86730614methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate수율 33%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-[(1S)-1-[[(2R)-2-hydroxy-3-methyl-butanoyl]amino]ethyl]benzoate (3.0 g, 10.7 mmol) and 2-phenoxyethyl methanesulfonate (2.32 g, 10.7 mmol) in dry THF (25 mL) is added sodium hydride (440 mg, 10.7 mmol). The mixture is stirred at room temperature overnight and partitioned between 1N HCl and EtOAc. The aqueous layer is extracted with EtOAc. The combined EtOAc layers are washed with brine, dried with MgSO4, filtered, and concentrated. The crude material (4.7 g) is purified using silica gel column chromatography (120 g cartridge; 30 to 100% ethyl acetate in heptane) to provide the title compound as a white solid (1.41 g, 33%). MS (m/z): 400.2 (M+1).

후처리

  1. custompartitioned between 1N HCl and EtOAc
  2. extractionThe aqueous layer is extracted with EtOAc
  3. washThe combined EtOAc layers are washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material (4.7 g) is purified

출처 및 근거

ORD 기록
ord-32aa475cc8b04a6fb13c55a44e2ff4e1
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000043B2

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