Trifluoroacetic acid → (1S,6R)-3,8-Diazabicyclo[4.2.0]octan-8-yl(2-fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl)methanone

HRID 2175000Notes

Reaction equation

HRID 2175000 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([N:25]2[N:29]=[CH:28][CH:27]=[N:26]2)[C:3]=1[C:4]([N:6]1[C@H:13]2[C@H:8]([CH2:9][CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12]2)[CH2:7]1)=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C@H:13]12[N:6]([C:4]([C:3]3[C:21]([N:25]4[N:26]=[CH:27][CH:28]=[N:29]4)=[CH:22][CH:23]=[CH:24][C:2]=3[F:1])=[O:5])[CH2:7][C@H:8]1[CH2:9][CH2:10][NH:11][CH2:12]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67086932(1S,6R)-tert-Butyl 8-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate

Product 1

HCID 67086546(1S,6R)-3,8-Diazabicyclo[4.2.0]octan-8-yl(2-fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1S,6R)-tert-butyl 8-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate (400 mg, 1.0 mmol) in CH2Cl2 (5 mL) was added TFA (5 mL). After the reaction was judged complete, the volatiles were removed under reduced pressure. The resulting residue was neutralized using 5% Na2CO3(aq) followed by extraction with CH2Cl2 (3×). The combined organics were dried (Na2SO4) and concentrated to give the title compound as an oil that was used without further purification.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. extractionfollowed by extraction with CH2Cl2 (3×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67e96bc5236a441db447d44ce039a747
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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