Trifluoroacetic acid → HCID 66701077, compound

HRID 2062083Notes

Reaction equation

HRID 2062083 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([Cl:26])=[CH:18][C:17]=2[C:27](=[O:38])[NH:28][C:29]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH3:32])[CH2:30][CH3:31])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:36]([O:35][C:33](=[O:34])[C:29]([NH:28][C:27]([C:17]1[CH:18]=[C:19]([Cl:26])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]=1[O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:38])([CH3:32])[CH2:30][CH3:31])[CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66701209HCID 66701209, compound

Product 1

HCID 66701077HCID 66701077, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.16 g of 4-[4-chloro-2-(1-ethoxycarbonyl-1-methyl-propylcarbamoyl)-naphthalen-1-yloxymethyl]-piperidine-1-carboxylic acid tert-butyl ester in 8 mL dichloromethane was added 4 mL of TFA at room temperature. This mixture was stirred at room temperature for 1 hour and then concentrated to dryness in vacuo. The residue was treated with 7 M NH3 in MeOH to adjust to pH 9. It was then chromatographed on silica with 7 N NH3 in MeOH/dichloromethane to provide 72 mg 2-{[4-chloro-1-(piperidin-4-yl-methoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. additionThe residue was treated with 7 M NH3 in MeOH
  3. customIt was then chromatographed on silica with 7 N NH3 in MeOH/dichloromethane

Sources & evidence

ORD record
ord-00cf273bfca5417788e241dea862500b
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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