Trifluoroacetic acid → HCID 68565462, compound

HRID 970365Notes

Reaction equation

HRID 970365 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][C@H:15]([OH:28])[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[N:24]=3)[N:19]=[CH:18][CH:17]=2)[C@H:10]([C:29]([F:32])([F:31])[F:30])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][C@@H:15]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[N:24]=3)[N:19]=[CH:18][CH:17]=2)[OH:28])[C@H:10]([C:29]([F:30])([F:32])[F:31])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68566703HCID 68566703, compound

Product 1

HCID 68565462HCID 68565462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{(2S,4S)-[(R)-hydroxy-(6-methoxy-[1,5]naphthyridin-4-yl)ethyl]-2-(trifluoromethyl)piperidin-4-yl}carbamic acid tert-butyl ester (1j) is dissolved in CH2Cl2 and TFA (1:1, v/v). After 2 hrs, the solution is concentrated to dryness under vacuum and the residue is redissolved in 4 M HCl in dioxane. After 30 min, the slurry is triturated with Et2O and filtered. The solid is dissolved in H2O and the solution is made basic with aqueous NaOH. The basic aqueous solution is concentrated to dryness under vacuum and the residue is dried under high vacuum. The resulting solid is extracted with CH2Cl2/MeOH (10:1, v/v), and the combined extracts are concentrated and dried under high vacuum to give the title compound.

Workup

  1. concentrationthe solution is concentrated to dryness under vacuum
  2. dissolutionthe residue is redissolved in 4 M HCl in dioxane
  3. waitAfter 30 min
  4. customthe slurry is triturated with Et2O
  5. filtrationfiltered
  6. dissolutionThe solid is dissolved in H2O
  7. concentrationThe basic aqueous solution is concentrated to dryness under vacuum
  8. customthe residue is dried under high vacuum
  9. extractionThe resulting solid is extracted with CH2Cl2/MeOH (10:1
  10. concentrationv/v), and the combined extracts are concentrated
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-49af3ef554134880890e1697c968ca9d
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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