Dimethylformamide → methyl N-[(pent-4-enyloxy)carbonyl]-norleucinate

HRID 1423348노트

반응식

HRID 1423348 반응식
[CH2:1]=[CH:2][CH2:3][CH:4]([OH:6])C.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].Cl.[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][CH2:27][CH3:28])[NH2:24].[CH3:30]N(C=O)C>CCOCC>[CH2:4]([O:6][C:7]([NH:24][C@H:23]([C:22]([O:21][CH3:20])=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:8])[CH2:3][CH2:2][CH:1]=[CH2:30]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 122474-Penten-2-OLHCID 682631,1'-CarbonyldiimidazoleHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

생성물 1

HCID 45378375methyl N-[(pent-4-enyloxy)carbonyl]-norleucinate수율 74%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 1-penten-4-ol (0.95 g, 11.0 mmol) in DMF (15 mL) at 0° C. was added carbonyldiimidazole (1.79 g, 11.0 mmol). The reaction mixture was warmed to RT and stirred for 30 min. L-norleucine methyl ester hydrochloride (2.0 g, 11.0 mmol) was then added, the reaction mixture was heated to 50° C. and stirred for 15 min. Upon cooling, the reaction mixture was diluted with Et2O and washed twice with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient elution 10 to 90% EtOAc in hexanes) to afford 2.1 g (74%) methyl N-[(pent-4-en-1-yloxy)carbonyl]-L-norleucinate as a clear oil.

후처리

  1. temperaturethe reaction mixture was heated to 50° C.
  2. stirringstirred for 15 min
  3. temperatureUpon cooling
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (gradient elution 10 to 90% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c9ba9eb07b334e60bd76cc94db3ae54c
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927569B2

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