Acetic Acid → HCID 22632587, 화합물

HRID 2417508노트

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HRID 2417508 반응식
[N+:1]([C:4]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:5]=1[CH2:6]C(N)C(OCC)=O)([O-])=O.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1.[CH2:32]([N:34](CC)CC)[CH3:33].[H][H].[N:41]1([C:46]([C:48]2[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=2)=[O:47])[CH2:45][CH:44]=[CH:43][CH2:42]1.C(O)(=[O:58])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.C(O)C.[OH-].[Na+].[Pd]>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:34]2[CH2:6][C:5]3[CH:14]=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:4]=3[N:1]([CH2:52][C:51]3[CH:54]=[CH:55][C:48]([C:46]([N:41]4[CH2:45][CH:44]=[CH:43][CH2:42]4)=[O:47])=[CH:49][CH:50]=3)[C:33](=[O:58])[CH2:32]2)=[O:28])=[CH:25][CH:24]=1

참가 물질

13

반응물 7

HCID 176Acetic AcidHCID 8471Triethylamine2회HCID 85014-Chlorobenzoyl chlorideHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589880HCID 86589880, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 22632587HCID 22632587, 화합물

시약·촉매·용매 5

HCID 23938Palladium촉매HCID 702Ethanol용매2회HCID 6344Dichloromethane용매5회HCID 8857Ethyl Acetate용매2회HCID 14798Sodium Hydroxide용매

실험 절차

1.6 g (5.2 mmol) of ethyl [2-nitro-4-(trifluoromethyl)benzyl]-aminoacetate was dissolved in 50 ml of dichloromethane. 0.8 ml (6.3 mmol) of 4-chlorobenzoyl chloride and 1.1 ml (7.8 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product was obtained. The crude product was dissolved in a mixture of 10 ml of ethyl acetate and 10 ml of ethanol. 160 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 4 hours. The reaction mixture was filtered through Celite. The solvent was evaporated and 87 mg (0.21 mmol) of the obtained crude product was dissolved in 10 ml of dichloromethane. 50 mg (0.25 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.25 ml (0.42 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 110 mg (0.53 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 5 ml of 1 N sodium hydroxide and 5 ml of ethanol, and the obtained solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 42 mg (0.25 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.04 ml (0.42 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated, and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

후처리

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. customThe solvent was evaporated
  5. custom87 mg (0.21 mmol) of the obtained crude product
  6. stirringwere stirred at room temperature for 30 minutes
  7. stirringwere stirred at room temperature overnight
  8. stirringthe obtained solution was stirred at room temperature for 5 hours
  9. stirringwere stirred overnight
  10. customThe solvent was evaporated
  11. customthe obtained crude product
  12. additionwas treated in the same manner as in step 3 in Example 1

출처 및 근거

ORD 기록
ord-5636c485278b45b99db36a40757b2329
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825191B2

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