Tetrabutylammonium Fluoride Trihydrate → (+/-)-3-[n,n-Bis(2-hydroxyethyl)amino]-1,2-bis(tetradecanoyloxy)propane

HRID 2191391노트

반응식

HRID 2191391 반응식
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:39][CH2:40][CH2:41][N:42]([CH2:63][CH:64]([O:82][C:83](=[O:97])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH3:96])[CH2:65][O:66][C:67](=[O:81])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])[CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.C(Cl)Cl>[OH:45][CH2:44][CH2:43][N:42]([CH2:63][CH:64]([O:82][C:83](=[O:97])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH3:96])[CH2:65][O:66][C:67](=[O:81])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])[CH2:41][CH2:40][OH:39]

참가 물질

5

반응물 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131730103HCID 131730103, 화합물

생성물 1

HCID 91576435(+/-)-3-[n,n-Bis(2-hydroxyethyl)amino]-1,2-bis(tetradecanoyloxy)propane수율 72%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Another batch of XV was prepared as follows: tetrabutyl ammonium fluride trihydrate (0.50 g, 1.60 mmol) was added to an ice-cooled solution of XIV (0.43 g, 0.40 mmol) in THF (3 mL) under N2 atmosphere. The reaction mixture was allowed to warm up to room temperature. After stirring overnight at room temperature, the reaction mixture was diluted with CH2Cl2 (30 mL) and sequentially washed with 5% NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 2% methanol in CHCl3) furnished XV (172 mg, 72%) as a wax. NMR spectra coordinates are as follows: 1H NMR (CDCl3): δ 5.24-5.14 (m, 1H), 4.35 (dd, J=12.0, 3.2 Hz, 1H), 4.10 (dd, J=12.4, 6.4 Hz, 1H), 3.60 (t, J=5.2 Hz, 4H), 2.77-2.66 (m, 6H), 2.38-2.26 (m, 4H), 1.66-1.54 (m, 4H), 1.36-1.18 (m, 40H), 0.87 (t, J=6.0 Hz, 6H).

후처리

  1. customAnother batch of XV was prepared
  2. washsequentially washed with 5% NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washby column chromatography (SiO2, elution with 2% methanol in CHCl3)

출처 및 근거

ORD 기록
ord-a1be7d9e93d14ade99ade6048dfc9110
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329681B2

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