tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate → tert-Butyl N-allyl-N-[2-oxo-2-(2-thienyl)ethyl]carbamate

HRID 338079노트

반응식

HRID 338079 반응식
[CH2:1]([N:4]([CH2:12][C:13](N(OC)C)=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[Li]>O1CCCC1>[CH2:1]([N:4]([CH2:12][C:13](=[O:14])[C:20]1[S:19][CH:23]=[CH:22][CH:21]=1)[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 86697892tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamateHCID 178418439HCID 178418439, 화합물

생성물 1

HCID 86697895tert-Butyl N-allyl-N-[2-oxo-2-(2-thienyl)ethyl]carbamate수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate (25 g, 96.8 mmol) in tetrahydrofuran (339 mL) at −78° C. is added drop wise 2-thienyllithium (145 ml, 1 M in tetrahydrofuran) over 20 min. The reaction is carefully quenched with aqueous ammonium chloride (20 mL), diluted with water (100 mL), and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1) to give the title compound (15.2 g, 56%). ES/MS (m/e): 182 (M+H-100).

후처리

  1. customThe reaction is carefully quenched with aqueous ammonium chloride (20 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue is purified by silica gel flash chromatography
  9. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-f68aa4a492dd4f91b1e8023167a98ad7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889856B2

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