Dimethyl Sulfoxide → Benzyl N-methyl-N-(2-oxoethyl)carbamate

HRID 871210노트

반응식

HRID 871210 반응식
CS(C)=O.CCN(C(C)C)C(C)C.[CH2:14]([O:21][C:22]([N:24]([CH2:26][CH2:27][OH:28])[CH3:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[CH2:14]([O:21][C:22]([N:24]([CH2:26][CH:27]=[O:28])[CH3:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 13279869N-Cbz-N-methyl-2-aminoethanol

생성물 1

HCID 12010768Benzyl N-methyl-N-(2-oxoethyl)carbamate수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

DMSO (71 mL, 1 mol) and DIPEA (87.1 mL, 0.5 mol) were added to a stirred solution of the product of step (a) (20.9 g, 0.1 mol) in dichloromethane (200 mL) at −10° C. The reaction mixture was stirred at −10° C. for 15 min and then sulfur trioxide pyridine complex (79.6 g, 0.5 mol) was added and the resulting mixture was stirred for 1 hour. The reaction mixture was quenched with addition of 1M hydrochloric acid (200 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried (potassium carbonate) and solvent removed under reduced pressure to give the title compound (20.7 g, ˜100% yield).

후처리

  1. additionsulfur trioxide pyridine complex (79.6 g, 0.5 mol) was added
  2. stirringthe resulting mixture was stirred for 1 hour
  3. customThe reaction mixture was quenched with addition of 1M hydrochloric acid (200 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium bicarbonate (100 mL), brine (100 mL)
  6. dry with materialdried (potassium carbonate) and solvent
  7. customremoved under reduced pressure

출처 및 근거

ORD 기록
ord-fe4eeb479c9240408b7063291feaca0d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969571B2

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