Trifluoroacetic acid → HCID 54925194, compound

HRID 1092335Notes

Reaction equation

HRID 1092335 reaction equation
C(OC(=O)[NH:7][C:8]1([C:13](=[O:25])[NH:14][CH:15]2[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]2[CH2:17]4)[CH2:21]3)[CH2:12][CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:16]12[CH2:17][CH:18]3[CH2:19][CH:20]([CH2:21][CH:22]([CH2:23]3)[CH:15]1[NH:14][C:13]([C:8]1([NH2:7])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:25])[CH2:24]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66593356HCID 66593356, compound

Product 1

HCID 54925194HCID 54925194, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(adamantan-2-ylcarbamoyl)-cyclopentyl]-carbamic acid tert-butyl ester (710 mg) in DCM (10 mL) was added TFA (1.5 mL) at 0° C. The mixture was stirred and allowed to warm to RT over night. The reaction mixture was evaporated and the residue was re-dissolved in DCM and washed with saturated NaHCO3 and brine. The organic layer was dried with Na2CO2 and evaporated to give a residue that was purified by flash chromatography using ethyl acetate as an eluent to give the desired material as a colorless glass (377 mg). MS (ESI): 263.4 (MH+).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was re-dissolved in DCM
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried with Na2CO2
  5. customevaporated
  6. customto give a residue that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-1c9cc0ede6c54c02991b1b8c8e73b657
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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