Dimethyl Sulfate → tert-Butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate

HRID 2093019ノート

反応式

HRID 2093019 の反応式
[CH2:1]([NH:8][C:9](=[O:21])[C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:24]OS(OC)(=O)=O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([NH:8][C:9](=[O:21])[C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:11][O:12][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 46223140tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamate

生成物 1

HCID 46223141tert-Butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate収率 109%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒3 回HCID 1140Toluene溶媒

反応条件

温度
10 °C

実験手順

To a stirred solution of 3.2 g (0.01 mol) of Intermediate 4 in 50 mL of toluene was added 0.61 g of tetrabutylammonium bromide and 5 ml of water. The resulting mixture was cooled to 10° C. and a solution of 2.4 g of sodium hydroxide in 2.5 ml of water was added dropwise maintaining the temperature below 10° C. Then, 5.54 g of dimethylsulfate was added dropwise maintaining the temperature below 10° C. After stirring at 10° C. for 2 hours, water (80 mL) was added and the reaction stirred at room temperature overnight. The layers were separated and the aqueous layer was washed twice with dichloromethane (50 mL). The combined organic phase was washed with sodium bicarbonate solution (2×30 mL) and brine. The solvent was removed under vacuum yielding 3.36 g of a pale red-oil. The oil was not purified and used directly in the following step.

後処理

  1. temperaturemaintaining the temperature below 10° C
  2. temperaturemaintaining the temperature below 10° C
  3. stirringthe reaction stirred at room temperature overnight
  4. customThe layers were separated
  5. washthe aqueous layer was washed twice with dichloromethane (50 mL)
  6. washThe combined organic phase was washed with sodium bicarbonate solution (2×30 mL) and brine
  7. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-ab83edf02a53442f96d8bbfcd95bcdf5
出典データセット
uspto-grants-2013_05
特許番号
US08440861B2

反応ノート

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