Sodium hydride → HCID 86707440, 화합물

HRID 338898노트

반응식

HRID 338898 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CS(O[CH2:31][CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=O)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:31][CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 14555479Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylateHCID 184649242-[(2-Methylpropan-2-yl)oxy]ethyl methanesulfonate

생성물 1

HCID 86707440HCID 86707440, 화합물수율 88%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (S)-benzyl 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate (2.50 g, 7.80 mmol) in anhydrous DMF (20 mL) cooled to 0° C. in an ice bath was added a 60% dispersion of sodium hydride in mineral oil (0.47 g, 11.7 mmol). The mixture was allowed to warm to ambient temperature and stirred for 1 hour. 2-tert-Butoxyethyl methanesulfonate (2.3 g, 11.7 mmol) was added and the mixture was stirred at 0° C. in an ice bath, then allowed to slowly warm to ambient temperature and stirred for 18 hours. The mixture was partitioned between water (50 mL) and ethyl acetate (100 mL). The layers were separated and washed with aqueous 1N HCl, water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage, 40M; 20% ethyl acetate/hexane) to afford (S)-benzyl 3-(tert-butoxycarbonyl(2-tert-butoxyethyl)amino)pyrrolidine-1-carboxylate (2.87 g, 88%).

후처리

  1. stirringthe mixture was stirred at 0° C. in an ice bath
  2. temperatureto slowly warm to ambient temperature
  3. stirringstirred for 18 hours
  4. customThe mixture was partitioned between water (50 mL) and ethyl acetate (100 mL)
  5. customThe layers were separated
  6. washwashed with aqueous 1N HCl, water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (Biotage, 40M; 20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-00d6589429e44f488ef098e0331f8a58
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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