Trifluoroacetic acid → HCID 86709515, compound

HRID 1848505Notes

Reaction equation

HRID 1848505 reaction equation
C(OC([NH:8][CH:9]([CH3:29])[CH:10]([C:12]1([C:25](OC)=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[OH:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+].O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>C(Cl)Cl>[OH:11][CH:10]1[C:12]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:25](=[O:26])[NH:8][CH:9]1[CH3:29]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 86709514HCID 86709514, compound

Product 1

HCID 86709515HCID 86709515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-tert-butyl 4-methyl 4-(2-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)piperidine-1,4-dicarboxylate (8000 mg, 19.2 mmol) in DCM (190 mL) was added TFA (44.4 mL, 576 mmol) at 0° C. and the resulting solution was stirred for 2 h. After removing the volatiles, high vacuum was applied briefly to remove excess TFA, and the residue was dissolved in MeOH (190 mL), and K2CO3 (26.5 g, 192 mmol) was added. The reaction mixture was heated at 60° C. for 2 h. After cooling to room temperature, saturated NaHCO3 solution (60 mL) was added, followed by (BOC)2O (12.6 g, 57.6 mmol). The reaction mixture was stirred overnight, and extracted with DCM. The organic layer was dried with MgSO4, and concentrated to give the crude product, which was purified by column chromatography (0-20% MeOH/DCM, monitored at 210 nM) to give the title compound. LC/MS: [(M+1)]+=285

Workup

  1. customAfter removing the volatiles, high vacuum
  2. customto remove excess TFA
  3. dissolutionthe residue was dissolved in MeOH (190 mL)
  4. temperatureAfter cooling to room temperature
  5. stirringThe reaction mixture was stirred overnight
  6. extractionextracted with DCM
  7. dry with materialThe organic layer was dried with MgSO4
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by column chromatography (0-20% MeOH/DCM, monitored at 210 nM)

Sources & evidence

ORD record
ord-392fdf9ebd6e47998f697253f37529b6
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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