Trifluoroacetic acid → HCID 68585006、化合物

HRID 17566ノート

反応式

HRID 17566 の反応式
FC(F)(F)C(O)=O.[C:8]([C:10]1[C:15]2[N:16]=[C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][C:25](C)(C)C)=[O:23])[O:18][C:14]=2[C:13]([N:29]2[CH2:33][CH2:32][C@H:31]([N:34]([CH3:36])[CH3:35])[CH2:30]2)=[C:12]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:11]=1[CH3:43])#[N:9].S(Cl)(Cl)=O>ClCCl>[C:8]([C:10]1[C:15]2[N:16]=[C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[O:18][C:14]=2[C:13]([N:29]2[CH2:33][CH2:32][C@H:31]([N:34]([CH3:35])[CH3:36])[CH2:30]2)=[C:12]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:11]=1[CH3:43])#[N:9]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 24386Thionyl ChlorideHCID 68587064tert-Butyl N-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-beta-alaninate

生成物 1

HCID 68585006HCID 68585006、化合物収率 17.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (1 ml) was added to a dichloromethane (2 ml) solution of tert-butyl N-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-β-alaninate (I-279) (51 mg, 0.104 mmol), followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in dichloromethane (1 ml), and at room temperature, thionyl chloride (10 μl, 0.138 mmol) was added, followed by stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, the then dissolved in chloroform, and washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine. After drying over anhydrous sodium sulfate and concentration, the insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1, v/v), the eluate was purified in slurry with diethyl ether to obtain the entitled compound (8.00 mg, 17%) as a pale yellow solid.

後処理

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (1 ml)
  4. stirringby stirring at room temperature for 1 hour
  5. customThe reaction liquid
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionthe then dissolved in chloroform
  8. washwashed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  9. dry with materialAfter drying over anhydrous sodium sulfate and concentration
  10. customthe insoluble matter was separated by filtration
  11. customthe solvent was evaporated away
  12. customthe resulting residue was purified by preparative TLC (eluent, chloroform
  13. custommethanol=20:1, v/v), the eluate was purified in slurry with diethyl ether

出典と根拠

ORDレコード
ord-963859cd586346fb9f4b4013c677862a
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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