Trifluoroacetic acid → HCID 64129604, compound

HRID 1023426Notes

Reaction equation

HRID 1023426 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH:15]([OH:23])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][CH:15]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[OH:23])[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69082872[4-(2-Hydroxy-2-p-tolyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 64129604HCID 64129604, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of [4-(2-hydroxy-2-p-tolyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (80 mg, 0.24 mmol) in DCM (2 mL) is added trifluoroacetic acid (0.5 mL). The mixture is stirred for 30 min at room temperature. Then saturated NaHCO3 aquaous solution (10 mL) is added slowly and the resulting mixture is extracted with DCM (2×10 mL). All the organic layers are combined and concentrated. The crude is purified by silica flash column chromatography eluting with EtOAc in Heptane (gradient from 0% to 100%) to give 40 mg of the desired product.

Workup

  1. extractionthe resulting mixture is extracted with DCM (2×10 mL)
  2. concentrationconcentrated
  3. customThe crude is purified by silica flash column chromatography
  4. washeluting with EtOAc in Heptane (gradient from 0% to 100%)

Sources & evidence

ORD record
ord-92fedfb9c735406cb5a6f2193bae74b1
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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