Triethylamine → Methyl 5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-{[(prop-2-en-1-yloxy)-carbamoyl]amino}benzoate

HRID 535451

반응식

HRID 535451 반응식
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:34]3[C:29]([CH:30]=[CH:31][CH:32]=[CH:33]3)=[C:28]([O:35][CH3:36])[C:27]=2[CH3:37])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[CH2:38]([O:41][NH2:42])[CH:39]=[CH2:40].C(N(CC)CC)C>O1CCOCC1.O>[CH3:36][O:35][C:28]1[C:27]([CH3:37])=[C:26]([C:24]([C:21]2[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:42][O:41][CH2:38][CH:39]=[CH2:40])=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:25])[N:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[CH:33]2

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 420841O-AllylhydroxylamineHCID 66653263Methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate

생성물 1

HCID 86683451Methyl 5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-{[(prop-2-en-1-yloxy)-carbamoyl]amino}benzoate수율 160%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

0.251 g (0.83 mmol) of triphosgene diluted in 3 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 0.4 g (1.18 mmol) of methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate in 10 ml of dioxane. After stirring for 2.5 hours, 0.267 g (2.36 mmol) of O-prop-2-en-1-ylhydroxylamine and 0.82 ml (5.91 mmol) of triethylamine are added. The reaction medium is stirred for one hour and then hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is washed with a 1N aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium chloride, and then dried over sodium sulphate, filtered, and concentrated under reduced pressure. 0.581 g of a yellow solid is obtained.

후처리

  1. stirringThe reaction medium is stirred for one hour
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. customThe organic phase obtained
  4. washis washed with a 1N aqueous solution of hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5fbf785230f34dc8baeb183daea3150e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859544B2

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