Water → benzyl [(2S)-3-oxobutan-2-yl]carbamate

HRID 2275815노트

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HRID 2275815 반응식
CON(C)[C:4](=[O:18])[C@@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:6].[CH3:20][Mg]Br.C1COCC1.C1(C)C=CC=CC=1.O>C1COCC1>[O:18]=[C:4]([CH3:20])[C@@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:6]

참가 물질

6

반응물 4

HCID 962WaterHCID 10515879(S)-Benzyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamateHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 59895800benzyl [(2S)-3-oxobutan-2-yl]carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Under argon, 1000 mg of benzyl {(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (Example 148A, 3.8 mmol, 1 equivalent) were dissolved in 19.5 ml of THF and cooled to −78° C. At this temperature, 4 ml of 1.4 M methylmagnesium bromide solution in 1:3 THF/toluene (6 mmol, 1.5 equivalents) were added slowly. The mixture was stirred at −78° C. for 5 min and at RT for 1 h and allowed to stand at RT overnight. 0.27 ml of water was then added with ice cooling, and the mixture was concentrated. The residue was diluted with water and 1 N aqueous hydrochloric acid solution and extracted four times with ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. This gave 813 mg (88% of theory; purity 90%) of the title compound.

후처리

  1. waitto stand at RT overnight
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted with water and 1 N aqueous hydrochloric acid solution
  4. extractionextracted four times with ethyl acetate
  5. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8a1dd8e04e044e0c9fb4deb404043ff8
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126998B2

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