Trifluoroacetic acid → HCID 68585006, compound

HRID 17566Notes

Reaction equation

HRID 17566 reaction equation
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]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24386Thionyl ChlorideHCID 68587064HCID 68587064, compound

Product 1

HCID 68585006HCID 68585006, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-963859cd586346fb9f4b4013c677862a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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