Trifluoroacetic acid → HCID 66664373, compound

HRID 1773586Notes

Reaction equation

HRID 1773586 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]([O:18][CH:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)(C)(C)C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[OH-].[Na+]>ClCCl>[NH2:7][C:8]1[C:17]([O:18][CH:19]2[CH2:20][CH2:21][CH:22]([OH:25])[CH2:23][CH2:24]2)=[CH:16][C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2.[NH2:7][C:8]1[C:17]([O:18][CH:19]2[CH2:24][CH2:23][CH:22]([O:30][C:29](=[O:31])[C:28]([F:33])([F:32])[F:27])[CH2:21][CH2:20]2)=[CH:16][C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66664907HCID 66664907, compound

Product 2

HCID 66664373HCID 66664373, compoundHCID 66664730HCID 66664730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [3-(4-hydroxy-cyclohexyloxy)-naphthalen-2-yl]-carbamic acid tert-butyl ester (0.15 g, 0.58 mmol) and trifluoroacetic acid (0.2 mL) in dichloromethane (5 mL) was stirred at room temperature for 16 hours. The reaction mixture was basified by addition of an aqueous solution of sodium hydroxide and was extracted twice with dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 75/25) to give 38 mg of 4-(3-amino-naphthalen-2-yloxy)-cyclohexanol and 66 mg of trifluoroacetic acid 4-(3-amino-naphthalen-2-yloxy)-cyclohexyl ester. The trifluoroacetate was treated with a solution of sodium hydroxide (11 mg) in ethanol (2 mL) and water and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was partitioned between water and dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford additional 40 mg of 4-(3-amino-naphthalen-2-yloxy)-cyclohexanol.

Workup

  1. extractionwas extracted twice with dichloromethane
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 75/25)

Sources & evidence

ORD record
ord-c9d4051fba9548b991c1f518ef1068e2
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…