1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-allyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 384424노트

반응식

HRID 384424 반응식
Cl.CN(C)CCCN=C=NCC.[CH2:13]([C:16]1[C:23]([F:24])=[C:22]([F:25])[C:19]([CH2:20][OH:21])=[C:18]([F:26])[C:17]=1[F:27])[CH:14]=[CH2:15].[C:28]([C:30]([CH3:40])=[CH:31][C@@H:32]1[C@@H:34]([C:35](O)=[O:36])[C:33]1([CH3:39])[CH3:38])#[N:29]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:28]([C:30]([CH3:40])=[CH:31][C@@H:32]1[C@@H:34]([C:35]([O:21][CH2:20][C:19]2[C:18]([F:26])=[C:17]([F:27])[C:16]([CH2:13][CH:14]=[CH2:15])=[C:23]([F:24])[C:22]=2[F:25])=[O:36])[C:33]1([CH3:39])[CH3:38])#[N:29]

참가 물질

6

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12944013[2,3,5,6-Tetrafluoro-4-(prop-2-en-1-yl)phenyl]methanolHCID 66664531(1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

생성물 1

HCID 866520804-allyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate수율 94%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매

실험 절차

Under a nitrogen atmosphere, 0.23 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a mixture of 0.20 g of 4-allyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.16 g of (1R)-trans-3-(2-cyano-1-propeny)-2,2-dimethylcyclopropanecarboxylic acid, 0.05 g of 4-dimethylaminopyridine and 4 ml of anhydrous chloroform, and the mixture was stirred at room temperature for 3 hours. Thereafter, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate two times. Ethyl acetate layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.32 g of 4-allyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate represented by the following formula:

후처리

  1. extractionfollowed by extraction with ethyl acetate two times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dd8a666b1c884c8da9dcb7c59fd1b851
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367724B2

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