Trifluoroacetic acid → HCID 9903131, compound

HRID 2299336Notes

Reaction equation

HRID 2299336 reaction equation
C([O:5][C:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:24](=[O:28])[CH2:23][CH2:22][C:21]([CH3:30])([CH3:29])[C:20]=3[CH:19]=2)=[O:17])=[CH:11][CH:10]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>ClCCl>[C:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:24](=[O:28])[CH2:23][CH2:22][C:21]([CH3:30])([CH3:29])[C:20]=3[CH:19]=2)=[O:17])=[CH:13][CH:14]=1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 129717148,8-Dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid 4-(tert-butoxycarbonylmethyl)phenyl ester2×

Product 1

HCID 9903131HCID 9903131, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 4-(tert-butoxycarbonylmethyl)phenyl ester (Compound 19, 0.11 g, 0.229 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (0.85 mL and stirred at ambient temperature for 2.5 h. The volatiles were distilled off in vacuo and the residue was diluted with water and extracted with ethyl acetate (×3). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a solid which was subjected to flash column chromatography over silica gel (230-400 mesh) using ethyl acetate as the eluent to afford the title compound (0.024 g, 25%).

Workup

  1. distillationThe volatiles were distilled off in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a solid which

Sources & evidence

ORD record
ord-ef3ac232ccc343738d20a52999abe4fd
Source dataset
uspto-grants-2002_12
Patent number
US06495552B2

Reaction notes

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