Dicyclohexylcarbodiimide → 1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 2-[(1,1-dimethylethoxy)carbonyl]-hydrazide

HRID 1252596노트

반응식

HRID 1252596 반응식
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([C:16]([OH:18])=O)=[CH:3]1.[C:19]([O:23][C:24]([NH:26][NH2:27])=[O:25])([CH3:22])([CH3:21])[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.CN(C1C=CC=CN=1)C.ON1C2C=CC=CC=2N=N1>[CH3:20][C:19]([CH3:22])([O:23][C:24]([NH:26][NH:27][C:16]([C:4]1[NH:5][CH:6]=[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:2](=[O:1])[CH:3]=1)=[O:18])=[O:25])[CH3:21]

참가 물질

7

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 70091tert-Butyl carbazateHCID 110539185-(Benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxylic acid

생성물 1

HCID 141824661,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 2-[(1,1-dimethylethoxy)carbonyl]-hydrazide수율 77.4%

시약·촉매·용매 3

HCID 218852-Dimethylaminopyridine촉매HCID 757711-Hydroxybenzotriazole촉매HCID 6228Dimethylformamide용매2회

실험 절차

1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid (61.3 g, 0.25 mol) was suspended in 500 ml of dimethylformamide at room temperature, followed by the addition of 39.65 g (0.3 mol) of N-(t-butoxycarbonyl)hydrazine, 1.5 g of dimethylaminopyridine and 2.0 g of N-hydroxybenzotriazole, and the mixture was stirred for 30 minutes at room temperature. Then, 57.7 g (0.28 mol) of dicyclohexylcarbodiimide, dissolved in 100 ml of dimethylformamide, was added dropwise with stirring over 30 minutes, and the mixture was stirred at room temperature overnight. The precipitate (dicyclohexylurea) was filtered off and the filtrate evaporated in vacuo. The remaining syrup crystallized on treatment with diluted sodium bicarbonate solution. The dried crude product was recrystallized from 2 liters of ethyl acetate to yield 69.5 g of the title compound, melting point 173°-175° C. A second crop was obtained after evaporation of the mother liquor; 3.2 g, melting point 160°-165° C.

후처리

  1. additionwas added dropwise
  2. stirringwith stirring over 30 minutes
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationThe precipitate (dicyclohexylurea) was filtered off
  5. customthe filtrate evaporated in vacuo
  6. customThe remaining syrup crystallized on treatment with diluted sodium bicarbonate solution
  7. customThe dried crude product
  8. customwas recrystallized from 2 liters of ethyl acetate

출처 및 근거

ORD 기록
ord-88c563f3c1804baeae3e636de3172f8e
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04743685

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