Triethylamine → N-oleoyl-D-serine

HRID 1196069

반응식

HRID 1196069 반응식
S([O-])(OC(C)(C)S(OC1C=CC(O)=CC=1)(=O)=O)(=O)=O.[C:20]([OH:39])(=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:55][C@@H:56]([C:59]([OH:61])=[O:60])[CH2:57][OH:58].C(N(CC)CC)C>C(#N)C.O>[C:20]([NH:55][C@@H:56]([C:59]([OH:61])=[O:60])[CH2:57][OH:58])(=[O:39])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 71077D-SerineHCID 445639Oleic AcidHCID 867457864-Hydroxyphenyldimethylsulfomethyl sulfate

생성물 1

HCID 86745788N-oleoyl-D-serine수율 40.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매2회

반응 조건

온도
0 °C

실험 절차

4-hydroxyphenyldimethylsulfomethyl sulfate 2.66 g (0.01 mol) was heated and dissolved in 40 ml of acetonitrile. Oleic acid 2.82 g (0.01 mol) was added to the solution obtained, and the mixture was stirred at 0° C. To the mixture solution, dicyclohexyl carbodiimide 2.06 g (0.01 mol) was added little by little, and the solution was stirred for 2 hours at 0° C. and then for 2 hours at room temperature. The solution reacted was filtered to remove dicyclohexyl urea, and the filtrate was distilled in vacuo to obtain oily residue. D-serine 1.05 g (0.01 mol) and triethyl amine 1.4 ml (0.01 mol) were added to 10 ml of water. An acetonitrile solution of the above oily residue was added to the mixture with stirring, and stirred for 10 hours at room temperature. After reaction, the reaction mixture was concentrated under reduced pressure. The concentrate was adjusted to pH 2 or 3 with 6N-HCl, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium acetate, and freed of solvent in vacuo. The oily residue obtained was purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel and N-oleoyl-D-serine 1.5 g was obtained.

후처리

  1. customobtained
  2. stirringwas stirred for 2 hours at 0° C.
  3. customThe solution reacted
  4. filtrationwas filtered
  5. customto remove dicyclohexyl urea
  6. distillationthe filtrate was distilled in vacuo
  7. customto obtain oily residue
  8. stirringwith stirring
  9. stirringstirred for 10 hours at room temperature
  10. customAfter reaction
  11. concentrationthe reaction mixture was concentrated under reduced pressure
  12. extractionextracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with water
  14. dry with materialdried over anhydrous sodium acetate
  15. customThe oily residue obtained
  16. customwas purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel

출처 및 근거

ORD 기록
ord-591aa5c240de4bb69a7ae1a87f3afa6d
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112863

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