Water → N'-(2-chloro-4-fluoro-phenyl)-N'-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 1437870노트

반응식

HRID 1437870 반응식
C(N(CC)CC)C.[CH3:8][C@:9]12[C:15]([CH3:17])([CH3:16])[C@H:12]([CH2:13][CH2:14]1)[CH:11]([C:18](Cl)=[O:19])[C:10]2=[O:21].[C:22]([O:26][C:27]([NH:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[Cl:38])=[O:28])([CH3:25])([CH3:24])[CH3:23].O>ClCCl>[C:22]([O:26][C:27]([NH:29][N:30]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[Cl:38])[C:18]([CH:11]1[C:10](=[O:21])[C@@:9]2([CH3:8])[C:15]([CH3:17])([CH3:16])[C@@H:12]1[CH2:13][CH2:14]2)=[O:19])=[O:28])([CH3:25])([CH3:23])[CH3:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 57941306(1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl chloride2회HCID 57941334HCID 57941334, 화합물2회

생성물 1

HCID 57941348N'-(2-chloro-4-fluoro-phenyl)-N'-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester수율 90.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Triethylamine (21.3 mL, 153 mmol) was added in two portions to a cooled (0° C.) solution of (1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl chloride (Intermediate 20; 10.9 g, 51 mmol) in dichloromethane (100 mL), giving a thick suspension. Dichloromethane (30 mL) was added, followed by N′-(2-chloro-4-fluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (Intermediate 33; 9.8 g, 37.6 mmol). The reaction mixture was placed in an oil-bath at 50° C., heated at this temperature for 6 hours and then allowed to cool to room temperature and stir for 1 h. The reaction mixture was poured into water (200 mL) and two layers were separated. The organic layer was washed with water (2×200 mL) and brine (100 mL), dried (magnesium sulfate), filtered, evaporated, and then dried under high vacuum for 90 min to give N′-(2-chloro-4-fluoro-phenyl)-N′-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (14.9 g, 90%) as a pale foam.

후처리

  1. customgiving a thick suspension
  2. customThe reaction mixture was placed in an oil-bath at 50° C.
  3. temperatureheated at this temperature for 6 hours
  4. customwere separated
  5. washThe organic layer was washed with water (2×200 mL) and brine (100 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customdried under high vacuum for 90 min

출처 및 근거

ORD 기록
ord-1c21d9c0eb7d4231a05acf41213b3291
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622492B2

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