Triethylamine → HCID 178498697, 화합물

HRID 922348

반응식

HRID 922348 반응식
BrC(CBr)C(OC)=O.C(N(CC)CC)C.[C:16]1([C@@H:22]([N@:24]2[CH2:26][CH:25]2[C:27]([O:29][CH3:30])=[O:28])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[NH:24]1[CH2:26][CH:25]1[C:27]([O-:29])=[O:28].[C:16]1([C@@H:22]([N@:24]2[CH2:26][CH:25]2[C:27]([O:29][CH3:30])=[O:28])[CH3:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 95428Methyl 2,3-dibromopropionateHCID 178498697HCID 178498697, 화합물

생성물 2

HCID 3424444Aziridine-2-carboxylateHCID 178498697HCID 178498697, 화합물수율 37%

시약·촉매·용매 1

HCID 1140Toluene용매3회

실험 절차

To solution of methyl 2,3-dibromopropionate (25 mL, 198 mmol) in toluene at 5° C. was added triethylamine (55 mL, 0.39 mmol) in toluene (100 mL). After stirring for 5 min (S)-(1)-phenethylamine (25 mL, 198 mmol) in toluene (100 mL) was added dropwise. The suspension was refluxed for 3 h and allowed to cool down, filtered and the volatiles were evaporated under reduced pressure to give a residue that was purified by column chromatography (950 g of silica gel) with a gradient of 0-20% EtOAc in cyclohexane to yield to (S)-methyl 145)-1-phenylethyl)aziridine-2-carboxylate EBE 06044A as a yellow oil (17.31 g, 43% yield) and (R)-methyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate EBE 06044B as a yellow oil (15.14 g, 37% yield).

후처리

  1. additionwas added dropwise
  2. temperatureThe suspension was refluxed for 3 h
  3. temperatureto cool down
  4. filtrationfiltered
  5. customthe volatiles were evaporated under reduced pressure
  6. customto give a residue that
  7. customwas purified by column chromatography (950 g of silica gel) with a gradient of 0-20% EtOAc in cyclohexane

출처 및 근거

ORD 기록
ord-b03fe31c01694e43a2f41daeccbf997d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278943B2

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