Trifluoroacetic acid → HCID 68565447, compound

HRID 970371Notes

Reaction equation

HRID 970371 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[S:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=3[CH:26]=2)[C@H:10]([C:27]([F:30])([F:29])[F:28])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:30][C:27]([F:28])([F:29])[C@H:10]1[C@@H:11]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[S:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=3[CH:26]=2)[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68566704HCID 68566704, compound

Product 1

HCID 68565447HCID 68565447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R,4S)-4-[(3-oxo-3,4-dihydro-2H-benzo-[1,4]thiazin-6-ylmethyl)amino]-3-(trifluoromethyl)piperidine-1-carboxylic acid tert-butyl ester (2e) (1 equiv.) 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 dissolved 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 under vacuum and the residue is dried under high vacuum. The resulting solid is extracted with CH2Cl2/MeOH (10:1, v/v) and the solution is concentrated. The residue is dried under high vacuum to give the title compound.

Workup

  1. concentrationthe solution is concentrated to dryness under vacuum
  2. dissolutionthe residue is dissolved 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 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 solution is concentrated
  11. customThe residue is dried under high vacuum

Sources & evidence

ORD record
ord-1a85e41b2937489181a588a5d22be404
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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