Hydrazine → HCID 67437264、化合物

HRID 521366ノート

反応式

HRID 521366 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][NH2:21]>C(Cl)Cl>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]([NH:20][NH2:21])=[O:11])=[CH:14][CH:15]=1

参加物

4

反応物 2

HCID 9321HydrazineHCID 27567812-(((Tert-butoxy)carbonyl)amino)-2-(4-chlorophenyl)acetic acid

生成物 1

HCID 67437264HCID 67437264、化合物収率 72.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1,1-Carbonyldiimidazole (1.60 g, 9.89 mmol) was added to a solution of 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)acetic acid (2.57 g, 9.00 mmol) in CH2Cl2 (22.5 mL, 9.00 mmol), and the mixture was stirred for 30 minutes until gas evolution ceased. Hydrazine (0.367 mL, 11.7 mmol) was then added to this solution, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with CH2Cl2 and washed with NaHCO3 (10%). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by reversed-phase chromatography (Biotage SP4, 40+M, C18, 25% to 100% MeCN/H2O). Fractions containing product were poured into a separatory funnel and extracted with ethyl acetate (3×). The combined organic layers were dried and concentrated to give tert-butyl 1-(4-chlorophenyl)-2-hydrazinyl-2-oxoethylcarbamate as a solid (1.95 g, 72%). LCMS (APCI+) M+H+: 299 (5%); M+H+-Boc: 199 (100%); rt=2.78 minutes. 1H NMR (400 MHz, CDCl3) δ 7.73 (s, 1H), 7.30 (s, 4H), 5.85 (d, J=6.6 Hz, 1H), 5.21 (s, 1H), 3.87 (s, 2H), 1.42 (s, 9H).

後処理

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washwashed with NaHCO3 (10%)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by reversed-phase chromatography (Biotage SP4, 40+M, C18, 25% to 100% MeCN/H2O)
  6. additionFractions containing product
  7. additionwere poured into a separatory funnel
  8. extractionextracted with ethyl acetate (3×)
  9. customThe combined organic layers were dried
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-aa2cbf7ca7d7436cb2292863bd0cbaba
出典データセット
uspto-grants-2016_05
特許番号
US09328091B2

反応ノート

読み込み中…