Toluene → Methyl N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valinate

HRID 1511588노트

반응식

HRID 1511588 반응식
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH2:6].[C:12]([O-:15])(O)=O.[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH:28]([NH:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])([CH3:30])[CH3:29]>C1COCC1.CCOC(C)=O>[CH:28]([N:31]([CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[C:12]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8])=[O:15])([CH3:30])[CH3:29]

참가 물질

8

반응물 5

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 551578Isopropylpent-4-enylamineHCID 16217630Methyl L-tert-leucinate hydrochloride

생성물 1

HCID 57692708Methyl N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valinate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution (60 nM) of L-tert-leucine methyl-ester hydrochloride and NaHCO3 (8 eq) in dry THF, a solution 20% w/w of phosgene in toluene (5 eq) was added dropwise at 0° C. and the reaction mixture was stirred at that temperature for 30 minutes. Then the solid was filtered-off and the filtrate evaporated at reduced pressure. The resulting crude yellow oil was taken-up in dry THF (0.3 M) and added dropwise to a stirred solution (0.2 M) of N-isopropylpent-4-en-1-amine and TEA (1 eq). The reaction mixture was stirred at room temperature overnight. Then the mixture was taken-up in EtOAc and washed twice with water and brine. The organic phase was dried over Na2SO4 and the volatiles evaporated at reduced pressure. The crude was purified by flash chromatography eluting with petroleum ether (8) EtOAc (2) using Nynhydrin as stain. Methyl N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valinate was obtained as light yellow oil (43%).

후처리

  1. customthe filtrate evaporated at reduced pressure
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. washwashed twice with water and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe volatiles evaporated at reduced pressure
  6. customThe crude was purified by flash chromatography
  7. washeluting with petroleum ether (8) EtOAc (2)

출처 및 근거

ORD 기록
ord-e7292bffcf374dfe91155e0d3cc2db5c
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08216999B2

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