Potassium bisulfate → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 342626

反応式

HRID 342626 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10](=[O:27])[C@@H:11]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S([O-])(O)(=O)=O.[K+]>CCOCC.O>[C:23]([O:22][C:20]([NH:19][C@@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:10]=[O:27])=[O:21])([CH3:26])([CH3:24])[CH3:25]

参加物

6

反応物 3

HCID 516920Potassium bisulfateHCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-45 °C

実験手順

A mechanically stirred suspension of lithium aluminum hydride (6.59 g, 0.165 mol) in ether (1 L) was cooled to -45° C. under nitrogen. A solution of the product from Step A (0.150 mol) in ether (150 mL) was added, maintaining the temperature below -35° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -45° C. A solution of potassium hydrogen sulfate (36.1 g, 0.265 mol) in water was slowly added, maintaining the temperature below -5° C. After quenching, the reaction was stirred at room temperature for 1 h. The mixture was filtered through Celite, the ether evaporated, and the remainder partitioned between ethyl acetate and 2% potassium hydrogen sulfate. After washing with saturated brine, drying over magnesium sulfate and solvent removal, the title compound was obtained.

後処理

  1. temperaturemaintaining the temperature below -35° C
  2. additionWhen the addition
  3. temperaturethe reaction was warmed to 5° C.
  4. customrecooled to -45° C
  5. temperaturemaintaining the temperature below -5° C
  6. customAfter quenching
  7. filtrationThe mixture was filtered through Celite
  8. customthe ether evaporated
  9. customthe remainder partitioned between ethyl acetate and 2% potassium hydrogen sulfate
  10. washAfter washing with saturated brine
  11. dry with materialdrying over magnesium sulfate and solvent removal

出典と根拠

ORDレコード
ord-9076447184b9488f8a35983007bd93a5
出典データセット
uspto-grants-1999_01
特許番号
US05859012

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