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

HRID 871210ノート

反応式

HRID 871210 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fe4eeb479c9240408b7063291feaca0d
出典データセット
uspto-grants-2015_03
特許番号
US08969571B2

反応ノート

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