Trifluoroacetic acid → HCID 67608694, compound

HRID 1965221Notes

Reaction equation

HRID 1965221 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([C:11](=[O:42])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:38](=[O:41])[NH:39][CH3:40])[CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:40][NH:39][C:38]([N:25]1[CH2:26][CH:27]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=2)[CH:21]2[N:20]([C:18](=[O:19])[CH:13]([NH:12][C:11](=[O:42])[CH:9]([NH:7][CH3:6])[CH3:10])[C:14]([CH3:16])([CH3:17])[CH3:15])[CH2:24][CH2:23][CH:22]12)=[O:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67606947HCID 67606947, compound

Product 1

HCID 67608694HCID 67608694, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of carbamate 90 (175 mg, 0.29 mmol) in DCM (10 mL) was treated with TFA (4 mL) at 0° C. After 1.5 h, the reaction mixture was concentrated, diluted with EtOAc, washed successively with saturated aqueous NaHCO3, and brine dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by reverse phase HPLC (2″ Dynamax® C18; 10% ACN/water to 70% ACN/water containing 0.1% HOAc, 30 min; Flow: 40 mL/min). The product-containing fractions were combined, frozen, and lyophilized to afford 91 (80 mg, 55%) as a white flocculent solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed successively with saturated aqueous NaHCO3, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by reverse phase HPLC (2″ Dynamax® C18
  8. customto 70% ACN/water containing 0.1% HOAc, 30 min
  9. temperaturefrozen

Sources & evidence

ORD record
ord-edc149cf4fd14cbd84cfbcb552ec36e5
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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