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

HRID 1844770노트

반응식

HRID 1844770 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매3회HCID 1140Toluene용매

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5ac89074ed44cdc8b711a6c97e71aed
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946477B2

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