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

HRID 535451

反応式

HRID 535451 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5fbf785230f34dc8baeb183daea3150e
出典データセット
uspto-grants-2014_10
特許番号
US08859544B2

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