Triethylamine → 3-(Dimethylamino)propyl bis(2-((Z)-1-oxooctadec-9-enyloxy)ethyl)carbamate

HRID 1479327노트

반응식

HRID 1479327 반응식
[C:1]([O:20][CH2:21][CH2:22][NH:23][CH2:24][CH2:25][O:26][C:27](=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl.[C:47](=O)([O:55]C1C=CC([N+]([O-])=O)=CC=1)[O:48][CH2:49][CH2:50][CH2:51][N:52]([CH3:54])[CH3:53].C(N(CC)CC)C>C(Cl)(Cl)Cl>[O:19]=[C:1]([O:20][CH2:21][CH2:22][N:23]([CH2:24][CH2:25][O:26][C:27](=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:47](=[O:55])[O:48][CH2:49][CH2:50][CH2:51][N:52]([CH3:54])[CH3:53])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 233302823-(Dimethylamino)propyl 4-nitrophenyl carbonate hydrochloride2회HCID 86682231N,N-bis(2-((Z)-Octadec-9-enoyloxy)ethyl)amine

생성물 1

HCID 866996423-(Dimethylamino)propyl bis(2-((Z)-1-oxooctadec-9-enyloxy)ethyl)carbamate수율 22.2%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

반응 조건

온도
110 °C

실험 절차

Compound 73 (160 mg, 0.252 mmol) obtained in Example 73 was dissolved in chloroform (2.5 mL), and heat-stirred at 110° C. for 30 minutes with a microwave reactor after adding 3-(dimethylamino)propyl 4-nitrophenyl carbonate hydrochloride (115 mg, 0.379 mmol) synthesized according to the method described in Journal of American Chemical Society (J. Am. Chem. Soc.), 1981, Vol. 103, p. 4194-4199, and triethylamine (0.141 mL, 1.01 mmol). 3-(Dimethylamino)propyl 4-nitrophenyl carbonate hydrochloride (38.4 mg, 0.126 mmol) was added to the reaction mixture, and heat-stirred at 110° C. for 30 minutes with a microwave reactor. After being diluted with chloroform, the reaction mixture was washed with a 1 mol/L sodium hydroxide aqueous solution three times and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5) to give compound 116 (42.6 mg, 22.1%).

후처리

  1. customsynthesized
  2. stirringheat-stirred at 110° C. for 30 minutes with a microwave reactor
  3. washthe reaction mixture was washed with a 1 mol/L sodium hydroxide aqueous solution three times
  4. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationafter filtration
  7. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)

출처 및 근거

ORD 기록
ord-6238b9546fa64046a16cec66f3977883
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408914B2

반응 노트

불러오는 중…