Citric Acid → 4-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

HRID 228037

반응식

HRID 228037 반응식
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([OH:19])=O)([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)C#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:45][C:46]1[CH:53]=[CH:52][C:49]([NH:50][CH3:51])=[CH:48][CH:47]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([N:50]([C:49]3[CH:52]=[CH:53][C:46]([Cl:45])=[CH:47][CH:48]=3)[CH3:51])=[O:19])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

8

반응물 5

HCID 311Citric AcidHCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 702724-Chloro-N-methylbenzenamineHCID 231507384-{[(Tert-butoxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid

생성물 1

HCID 231505174-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

4-tert-Butoxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (101 mg) was dissolved in dichloromethane (2 mL). To this solution, trichloroacetonitrile (74.0 μL) and triphenylphosphine (196 mg) in dichloromethane (1.5 mL) were sequentially added and the mixture was stirred at room temperature for 2 hours. This was followed by addition of triethylamine (0.18 mL) and 4-chloro-N-methylaniline (98.6 μL) and stirring at room temperature for additional 5.5 hours. The reaction mixture was then poured into aqueous citric acid (5 mL) and was extracted with ethyl acetate (3×10 mL). The ethyl acetate extracts were combined, washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=2:1) to give 4-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (91.4 mg) as a white powder.

후처리

  1. stirringstirring at room temperature for additional 5.5 hours
  2. extractionwas extracted with ethyl acetate (3×10 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-3233b079ee80401286c5780430e054a0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560569B2

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