Trifluoroacetic acid → HCID 68585006, 화합물

HRID 17566노트

반응식

HRID 17566 반응식
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]

참가 물질

5

반응물 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

생성물 1

HCID 68585006HCID 68585006, 화합물수율 17.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-963859cd586346fb9f4b4013c677862a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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