Trifluoroacetic acid → 1365993-10-7

HRID 2366308Notes

Reaction equation

HRID 2366308 reaction equation
C(OC([NH:8][C:9]1[CH:18]=[C:17]([F:19])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Cl:20])[CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C:9]1[CH:18]=[C:17]([F:19])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Cl:20])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66801718HCID 66801718, compound

Product 1

HCID 668014661365993-10-7Yield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(tert-butoxycarbonylamino)-2-chloro-6-fluoro-benzoate (6.53 g, 21.5 mmol) in dichloromethane (40 mL) was added TFA (9.94 mL). The mixture was stirred at room temperature for 4 hours. The mixture was then concentrated. Water (30 mL) was added to the residue, and pH was adjusted 10 with 25% NaOH. The resulting suspension was extracted with EtOAc (3×). The combined organics were dried (Na2SO4), filtered and concentrated to give the title compound (4.41 g, quantitative yield) as an off-white solid. 1H NMR (400 MHz, CD2Cl2) δ 6.54 (s, 1H), 6.34 (dd, J=11.6, 2.1 Hz, 1H), 4.19 (s, 2H), 3.90 (s, 3H). LCMS (ESI) m/z 204.0 [M+H+].

Workup

  1. concentrationThe mixture was then concentrated
  2. additionWater (30 mL) was added to the residue, and pH
  3. extractionThe resulting suspension was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf8609d6afde4689a53e262ad4096f8b
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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