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

HRID 2275815ノート

反応式

HRID 2275815 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a1dd8e04e044e0c9fb4deb404043ff8
出典データセット
uspto-grants-2015_09
特許番号
US09126998B2

反応ノート

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