Water → benzyl (S)-2-(morpholin-4-yl)propionate

HRID 2068867

반응식

HRID 2068867 반응식
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Br[CH2:33][CH2:34][O:35][CH2:36][CH2:37]Br.O>CS(C)=O.C(OCC)(=O)C>[N:22]1([C@@H:21]([CH3:23])[C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:24])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 2802424L-Alanine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

생성물 1

HCID 13765076benzyl (S)-2-(morpholin-4-yl)propionate수율 66.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Under an argon atmosphere, to a solution of L-alanine benzyl ester tosylate (3.4 g, 9.7 mmol) and triethylamine (6.8 ml) in dimethyl sulfoxide (17 ml) was added a solution of 1-bromo-2-(2-bromoethoxy)ethane (1.5 ml, 12 mmol) in dimethyl sulfoxide (3 ml) under ice-cooling, and the mixture was stirred at room temperature for 24 hr. To the reaction solution were added water and ethyl acetate, and the organic layer was separated. Then, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (1.6 g, yield 64%).

후처리

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThen, the organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-7884a18d246b471885497e6efe81cae2
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299070B2

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