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

HRID 2191391ノート

反応式

HRID 2191391 の反応式
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]

参加物

5

反応物 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131730103HCID 131730103、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a1be7d9e93d14ade99ade6048dfc9110
出典データセット
uspto-grants-2012_12
特許番号
US08329681B2

反応ノート

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