Thionyl Chloride → tert-Butyl 4-((3,5-dimethoxy-4-methylbenzamido)methyl)-3-nitrobenzylcarbamate

HRID 1296773노트

반응식

HRID 1296773 반응식
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:17][CH3:18])[C:15]=1[CH3:16])[C:10]([OH:12])=O.[NH2:19][CH2:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:23][C:22]=1[N+:36]([O-:38])=[O:37]>CN(C=O)C.C1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([O:6][CH3:5])[C:15]=1[CH3:16])[C:10]([NH:19][CH2:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:23][C:22]=1[N+:36]([O-:38])=[O:37])=[O:12]

참가 물질

8

반응물 3

HCID 24386Thionyl ChlorideHCID 37644863,5-Dimethoxy-4-methylbenzoic acidHCID 86595905tert-Butyl 4-(aminomethyl)-3-nitrobenzylcarbamate

생성물 1

HCID 86595906tert-Butyl 4-((3,5-dimethoxy-4-methylbenzamido)methyl)-3-nitrobenzylcarbamate수율 100%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 241Benzene용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

DMF (2 drops) and thionyl chloride (0.080 mL, 1.1 mmol) were sequentially added to a suspension of 3,5-dimethoxy-4-methyl benzoic acid (0.0995 g, 0.507 mmol) in benzene (2 mL). The reaction mixture was heated at reflux for 2 h, and then concentrated. The residue was dissolved in dichloromethane (1 mL) and then added dropwise to a solution of compound 65c (0.144 g, 0.512 mmol) and TEA (0.2 mL, 1.4 mmol) in dichloromethane (1 mL). The reaction mixture was stirred overnight at rt. The mixture was diluted with ethyl acetate and washed with 0.1 N HCl (2×) and saturated sodium bicarbonate solution, dried, and concentrated to give compound 65d (0.233 g, 100%) as a yellow solid ESI-MS m/e 460.4 (M+1).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dichloromethane (1 mL)
  5. washwashed with 0.1 N HCl (2×) and saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8b8681b5c8754aa8a78b1315cb74837f
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07247654B2

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