Iodine → tert-butyl [(1S)-2-(4-ethylphenyl)-1-methyl-2-oxoethyl]carbamate

HRID 13015

반응식

HRID 13015 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.II.[C:13]([O:17][C:18]([NH:20][C@H:21]([C:23](N(OC)C)=[O:24])[CH3:22])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[C:13]([O:17][C:18](=[O:19])[NH:20][C@@H:21]([CH3:22])[C:23]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1)=[O:24])([CH3:16])([CH3:14])[CH3:15]

참가 물질

6

반응물 4

HCID 807IodineHCID 153131-Bromo-4-ethylbenzeneHCID 5462224MagnesiumHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

생성물 1

HCID 59339635tert-butyl [(1S)-2-(4-ethylphenyl)-1-methyl-2-oxoethyl]carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred suspension of magnesium turnings (243 mg, 10 mmol) in dry THF (10 ml) was added a solution of 1-bromo-4-ethylbenzene (1.85 g, 10 mmol) in dry THF (10 ml), followed by a small crystal of iodine. The reaction mixture was heated with reflux for 4 h, then cooled to r.t. A solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide (464 mg, 2 mmol) in dry THF (15 ml) was added dropwise, and the stirring was continued for 5 h at r.t. Then the reaction mixture was quenched with sat. aqueous NH4Cl (25 ml) stirred for 30 min, and the layers were separated. The aqueous layer extracted with ethyl acetate (50 ml). The combined organic layers were dried with Na2SO4, and the solvent was removed under reduced pressure to give the subtitle compound as colourless oil, 718 mg, 70% purity (as determined by NMR). Used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperaturewith reflux for 4 h
  3. customThen the reaction mixture was quenched with sat. aqueous NH4Cl (25 ml)
  4. customthe layers were separated
  5. extractionThe aqueous layer extracted with ethyl acetate (50 ml)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-2679ca58b8cc47999df1f52512ff3019
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728030B2

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