Trifluoroacetic acid → Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate

HRID 851943노트

반응식

HRID 851943 반응식
[C:1]([OH:7])(C(F)(F)F)=[O:2].[CH2:8]([N:15]1[CH:20]([C:21]([O:23]C(C)(C)C)=O)[CH2:19][CH2:18][CH2:17][NH:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:28](N(CC)CC)C>C(Cl)Cl>[O:23]=[C:21]([CH:20]1[CH2:19][CH2:18][CH2:17][NH:16][N:15]1[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:1]([O:7][CH3:28])=[O:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 18470069Tert-butyl 2-benzylperhydropyridazinecarboxylate

생성물 1

HCID 18470067Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate수율 72.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

반응 조건

온도
0 °C

실험 절차

20% TFA in CH2Cl2 was cooled to 0° C. and added dropwise to a solution of tert-butyl 2-benzylperhydropyridazinecarboxylate (13.34 g, 41.7 mmol) in 10 ml CH2Cl2. The mixture was stirred overnight. At this time, the mixture was cooled to 0° C. and 12.66 ml (125 mmol) triethylamine was added, followed by addition dropwise of methyl oxalyl chloride (5.62, 45.9 mmol) in 5 ml CH2Cl2. The mixture was allowed to stirred 2 hours at 0° C. and warmed up to room temperature overnight. The reaction was diluted with addition of CH2Cl2 and washed with water. The organic layer was dried over MgSO4, and filtered and concentrated. The crude product was further purified by silica chromatography to yield 9.2 g (72.4% yield) product as clear oil. 1H NMR (CDCl3, 400 MHz): δ 1.72 (m, 4H); 2.85 (m, 1H); 3.12 (m, 1H); 3.67 (s, 3H); 4.15 (m, 1H); 4.35 (m, 1H); 5.20 (m, 2H); 7.35 (m, 5H)

후처리

  1. stirringto stirred 2 hours at 0° C.
  2. temperaturewarmed up to room temperature overnight
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was further purified by silica chromatography

출처 및 근거

ORD 기록
ord-871fdc16df6543e5919d97f5200c76e3
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253169B2

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