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

HRID 1296773ノート

反応式

HRID 1296773 の反応式
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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8b8681b5c8754aa8a78b1315cb74837f
出典データセット
uspto-grants-2007_07
特許番号
US07247654B2

反応ノート

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