Succinic anhydride → 4-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid

HRID 1629658노트

반응식

HRID 1629658 반응식
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][N:9]([CH3:33])[CH2:10][CH:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:12][OH:13]>C1COCC1>[CH3:8][N:9]([CH3:33])[CH2:10][CH:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:12][O:13][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7]

참가 물질

4

반응물 2

HCID 7922Succinic anhydrideHCID 582643493-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol

생성물 1

HCID 583322974-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Succinic anhydride (0.60 g, 5.99 mmol, 1.1 equiv) was added in one portion to a dry THF (11 mL) solution of 3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol (2.0 g, 5.45 mmol, 1.0 equiv) and the resultant was refluxed for 18 hours under argon. The mixture was concentrated and then dissolved in EtOAc (10 mL) and poured into deionized water (20 mL). The layers were separated and the aqueous layer was extracted with two additional portions of EtOAc (25 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to provide crude 4-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid, a thick yellow oil, which was used without further purification.

후처리

  1. temperaturethe resultant was refluxed for 18 hours under argon
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in EtOAc (10 mL)
  4. additionpoured into deionized water (20 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with two additional portions of EtOAc (25 mL)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dbc37f6fb30847848921556800ffb696
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08790691B2

반응 노트

불러오는 중…