1-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate → (S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester

HRID 45587노트

반응식

HRID 45587 반응식
[O:1]=[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4][CH2:3]1.O.[C:20](=O)(O)[O-].[Na+]>O1CCCC1>[CH2:17]([O:16][C:14](=[O:15])[C@@H:5]([NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3][C:2](=[O:1])[CH3:20])[CH3:18]

참가 물질

4

반응물 2

HCID 54611861-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylateHCID 86585896Sodium bicarbonate water

생성물 1

HCID 58544329(S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (S)-1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate (7.00 g, 27.4 mmol) in tetrahydrofuran (100 mL) was added methyl Grignard reagent (3M in diethyl ether, 9.60 mL, 28.8 mmol) dropwise for 20 minutes at −78° C., and stirred for 1 hour. After stiffing for 2 hours at 0° C., to the mixture was added saturated sodium bicarbonate water dropwise, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (7.60 g, 26.5 mmol, 97%).

후처리

  1. waitAfter stiffing for 2 hours at 0° C., to the mixture
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-974ac14126504f90a5b89d96629da190
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541585B2

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