Trifluoroacetic acid → HCID 70098483, compound

HRID 467761Notes

Reaction equation

HRID 467761 reaction equation
C(OC([NH:8][C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][C:12]([CH2:15][O:16][CH3:17])=[CH:13][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH3:21][O:20][C:18]([C:10]1[C:9]([NH2:8])=[CH:14][CH:13]=[C:12]([CH2:15][O:16][CH3:17])[N:11]=1)=[O:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 70097589HCID 70097589, compound

Product 1

HCID 70098483HCID 70098483, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of methyl 3-(tert-butoxycarbonylamino)-6-(methoxymethyl)picolinate (695 mg, 2.35 mmol) at r.t. in dichloromethane (10 ml) under an argon atmosphere was added 2,2,2-trifluoroacetic acid (903 μl, 11.7 mmol) in one portion. The mixture was stirred at 50° C. overnight, then cooled to r.t. and treated carefully with 10% aq. Na2CO3 (10 ml). The aqueous solution was extracted with CH2Cl2 (10 ml). The combined organics were washed with brine (10 ml), dried over MgSO4, filtered and concentrated to leave the product as a light brown solid (424 mg, 92%) which was used for the next step without further purification.

Workup

  1. temperaturecooled to r.t.
  2. extractionThe aqueous solution was extracted with CH2Cl2 (10 ml)
  3. washThe combined organics were washed with brine (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bef4acfdb5947d6a4f956c41bf242f2
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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