Trifluoroacetic acid → HCID 68451633、化合物

HRID 1392788ノート

反応式

HRID 1392788 の反応式
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[NH:27][C:28]([C:30]1[N:31]=[CH:32][C:33]3[CH2:38][N:37]([C:39](OC(C)(C)C)=O)[CH2:36][C:34]=3[N:35]=1)=[O:29])=[O:19])=[CH:12]2>C(Cl)Cl>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[NH:27][C:28]([C:30]1[N:31]=[CH:32][C:33]3[CH2:38][N:37]([CH3:39])[CH2:36][C:34]=3[N:35]=1)=[O:29])=[O:19])=[CH:12]2

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58822249HCID 58822249、化合物

生成物 1

HCID 68451633HCID 68451633、化合物収率 51.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (1 ml) was added to a solution of the compound (34.0 mg) obtained in Example 32 dissolved in methylene chloride (1 ml) at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride (1 ml), to which triethylamine (17.6 μl), acetic acid (7.21 μl), 35% formalin (8.13 μl) and sodium triacetoxyborohydride (20.1 mg) were added at room temperature. The resultant mixture was stirred for 1 hour. Methylene chloride (10 ml) and saturated aqueous solution (10 ml) of sodium hydrogencarbonate were added to the reaction mixture to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:methylene chloride=7:93). A 1N ethanol solution of hydrochloric acid and ethyl acetate were added to the product thus obtained to solidify it, and the resultant solids were collected by filtration to obtain the title compound (8.0 mg).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (1 ml), to which triethylamine (17.6 μl), acetic acid (7.21 μl), 35% formalin (8.13 μl) and sodium triacetoxyborohydride (20.1 mg)
  3. additionwere added at room temperature
  4. stirringThe resultant mixture was stirred for 1 hour
  5. additionMethylene chloride (10 ml) and saturated aqueous solution (10 ml) of sodium hydrogencarbonate were added to the reaction mixture
  6. customto separate an organic layer
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (methanol:methylene chloride=7:93)
  10. additionA 1N ethanol solution of hydrochloric acid and ethyl acetate were added to the product
  11. customthus obtained
  12. filtrationthe resultant solids were collected by filtration

出典と根拠

ORDレコード
ord-233bee127a784e8c93dcfdbcf4858c8b
出典データセット
uspto-grants-2008_03
特許番号
US07342014B2

反応ノート

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