Trifluoroacetic acid → HCID 66670101, compound

HRID 1014924Notes

Reaction equation

HRID 1014924 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:24][C:20]1[CH:19]=[C:18]2[C:23]([C:15]([CH2:14][CH:9]3[CH:10]([CH3:13])[CH2:11][CH2:12][NH:8]3)=[CH:16][NH:17]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66670136HCID 66670136, compound

Product 1

HCID 66670101HCID 66670101, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution containing 66 (0.89 g, 0.0024 mol) in DCM (20 mL) at 0° C. was added TFA (4 mL). After 2 h, TLC analysis revealed complete consumption of 66 [10% MeOH/DCM, Rf(66)=0.7, Rf(67)=0.3]. The reaction mixture was concentrated in vacuo, diluted with DCM, washed with aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 0.6 g (86%) of 67 which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ9.0 (br s, 1H), 7.6-7.35 (m, 1H), 7.1-6.7 (m, 3H), 4.2 (br m, 1H), 3.2-2.5 (m, 5H), 2.1-1.2 (m, 3H), 1.05 (d, J=6.74 Hz, 3H) ppm.

Workup

  1. customconsumption of 66 [10% MeOH/DCM, Rf(66)=0.7
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with DCM
  4. washwashed with aqueous NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff207a6019b84ad094a7c7874bd1a256
Source dataset
uspto-grants-2011_07
Patent number
US07985735B2

Reaction notes

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