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

HRID 45587ノート

反応式

HRID 45587 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-974ac14126504f90a5b89d96629da190
出典データセット
uspto-grants-2013_09
特許番号
US08541585B2

反応ノート

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