Trifluoroacetic acid → HCID 10222859, compound

HRID 857381Notes

Reaction equation

HRID 857381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH:18](O)[CH3:19])=[CH:15][C:14]([F:21])=[CH:13][C:12]=3[N:11]3[CH2:22][CH2:23][CH:24]([CH2:25][C:26]([OH:28])=[O:27])[C:10]=23)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH2:18][CH3:19])=[CH:15][C:14]([F:21])=[CH:13][C:12]=3[N:11]3[CH2:22][CH2:23][CH:24]([CH2:25][C:26]([OH:28])=[O:27])[C:10]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 10112823HCID 10112823, compound

Product 1

HCID 10222859HCID 10222859, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+/−)-methyl [9-[(4-chlorophenyl)thio]-6-fluoro-8-(1-hydroxyethyl)-2,3-dihydro-1H-pytrolo[1,2-a]indol-1-yl]acetate (see Example 14, 85 mg) in CH2Cl2 were added trifluoroacetic acid (0.5 mL) and triethylsilane (0.2 mL). The mixture was stirred for 1 hour at r.t. and solvent was removed. The residue was purified by silica gel chromatography eluted with 30% EtOAc/hexane to give 70 mg of the title compound as a white foam which has hydrolyzed following the procedures described in Step 10 of Example 7.

Workup

  1. customsolvent was removed
  2. customThe residue was purified by silica gel chromatography
  3. washeluted with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-541681271fd24abda2e5f06b891b35a9
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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