Trifluoroacetic acid → 1-(4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}phenyl)ethanone

HRID 1964568Notes

Reaction equation

HRID 1964568 reaction equation
[C:1]([C:4]1[CH:39]=[CH:38][C:7]([O:8][C:9]2[CH:10]=[C:11]([C:21]3[N:22](C(OC(C)(C)C)=O)[C:23]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)=[CH:24][CH:25]=3)[CH:12]=[C:13]([O:15][C@@H:16]([CH3:20])[CH2:17][O:18][CH3:19])[CH:14]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH3:19][O:18][CH2:17][C@H:16]([CH3:20])[O:15][C:13]1[CH:14]=[C:9]([CH:10]=[C:11]([C:21]2[NH:22][C:23]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)=[CH:24][CH:25]=2)[CH:12]=1)[O:8][C:7]1[CH:38]=[CH:39][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66683501t-Butyl 2-{3-(4-acetylphenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

Product 1

HCID 580654701-(4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}phenyl)ethanoneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl 2-{3-(4-acetylphenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (73 mg, 0.133 mmol) synthesized in Example (39a) 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 2.5 hours. 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%-40%) to afford the desired compound (56 mg, yield 94%) as a pale yellow liquid.

Workup

  1. stirringstirring
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified
  4. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=30%-40%)

Sources & evidence

ORD record
ord-52fb425bb48a48c2abfaaf484c94d03a
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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