Trifluoroacetic acid → Methyl 4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoate

HRID 1964566Notes

Reaction equation

HRID 1964566 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:40]=[CH:39][C:8]([O:9][C:10]2[CH:11]=[C:12]([C:22]3[N:23](C(OC(C)(C)C)=O)[C:24]([C:27]4[S:28][CH:29]=[CH:30][N:31]=4)=[CH:25][CH:26]=3)[CH:13]=[C:14]([O:16][C@@H:17]([CH3:21])[CH2:18][O:19][CH3:20])[CH:15]=2)=[CH:7][CH:6]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:20][O:19][CH2:18][C@H:17]([CH3:21])[O:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:13]=1)[O:9][C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66683331t-Butyl 2-{3-[4-(methoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

Product 1

HCID 58065459Methyl 4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoateYield 112.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl 2-{3-[4-(methoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (70 mg, 0.124 mmol) synthesized in Example (38e) was dissolved in dichloromethane (1.0 mL). Trifluoroacetic acid (2.0 mL) was added dropwise with stirring under nitrogen atmosphere, and stirring was carried out at room temperature for 2 hours. The solvent was distilled off under reduced pressure, followed by dilution with ethyl acetate (30 mL), a saturated aqueous sodium hydrogencarbonate solution (20 mL) was added, and the solution was separated. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=30%-50%) to afford the desired compound (65 mg, yield ˜100%) as a pale yellow liquid.

Workup

  1. stirringstirring
  2. distillationThe solvent was distilled off under reduced pressure
  3. additiona saturated aqueous sodium hydrogencarbonate solution (20 mL) was added
  4. customthe solution was separated
  5. washThe organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified
  9. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=30%-50%)

Sources & evidence

ORD record
ord-dec34a650e3a4f59a942df8044956dc4
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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