Potassium Carbonate → Tert-butyl (1-phenylbut-3-yn-1-yl)carbamate

HRID 659131

반응식

HRID 659131 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH:10]=O)([CH3:4])([CH3:3])[CH3:2].[N+](=[C:21](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>CO>[C:12]1([CH:8]([NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][C:10]#[CH:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 15087934Tert-butyl N-(3-oxo-1-phenylpropyl)carbamate2회HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one2회

생성물 1

HCID 57429813Tert-butyl (1-phenylbut-3-yn-1-yl)carbamate수율 87.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To the solution of 1.2 g of tert-butyl 3-oxo-1-phenylpropylcarbamate (Formula 12) and 1.38 g of dimethyl 1-diazo-2-oxopropylphosphonate (Formula 15) in 60 mL of methanol at 0° C. was added 1.32 g of potassium carbonate. The mixture was stirred at room temperature for 16 hours then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane) gave 1.03 g (87%) of tert-butyl 1-phenylbut-3-ynylcarbamate (Formula 16) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.43 (s, 9H), 1.98-2.00 (m, 1H), 2.6-2.8 (m, 2H), 4.88 (br, 1H), 5.16 (br, 1H), 7.23-7.37 (m, 5H).

후처리

  1. customthen quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6e95369fee4741a88a46b9b467e411f2
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080570B2

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