Trifluoroacetic acid → HCID 10902815, compound

HRID 275776Notes

Reaction equation

HRID 275776 reaction equation
[O:1]1[CH2:21][C@@H:2]1[CH2:3][O:4][C:5]1[C:6](C=O)=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2.ClC1C=C(C=CC=1)[C:26]([O:28]O)=[O:27].FC(F)(F)C(O)=O>ClCCl>[O:1]1[CH2:21][C@@H:2]1[CH2:3][O:4][C:5]1[C:6]([O:28][CH:26]=[O:27])=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 15448801HCID 15448801, compound

Product 1

HCID 10902815HCID 10902815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A stirred solution of ethyl (R)-5-(2,3-epoxypropoxy)-4-formylindole-2-carboxylate (1.95 g; prepared by the method described above) in dichloromethane (40 ml) was cooled to 0° C. 3-Chloroperoxybenzoic acid (85%; 1.75 g) was then added in one portion followed by a solution of trifluoroacetic acid (0.77g) in dichloromethane (10 ml), in portions. The mixture was stirred at 0° C. for 10 minutes and then at ambient temperature for 1 hour. The reaction mixture was diluted with dichloromethane (300 ml) , washed successively with saturated aqueous sodium bisulphite solution (100 ml), saturated aqueous sodium bicarbonate solution (3×150 ml), dried over sodium sulphate and the solvent evaporated. The solid residue was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate to give ethyl (R)-5-(2,3-epoxypropoxy)-4-formyloxyindole-2-carboxylate (1.55 g) as a pale yellow crystalline solid; m.p. 123-125° C.

Workup

  1. customprepared by the method
  2. waitat ambient temperature for 1 hour
  3. washwashed successively with saturated aqueous sodium bisulphite solution (100 ml), saturated aqueous sodium bicarbonate solution (3×150 ml)
  4. dry with materialdried over sodium sulphate
  5. customthe solvent evaporated
  6. customThe solid residue was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate

Sources & evidence

ORD record
ord-009a4a4c99e64bf686b59082f18bad03
Source dataset
uspto-grants-2002_03
Patent number
US06353002B2

Reaction notes

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