Trifluoroacetic acid → HCID 57060556, compound

HRID 841928Notes

Reaction equation

HRID 841928 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:25][CH:26]1[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]1)=[O:24]>ClCCl>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:25][CH:26]1[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]1)=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57263454HCID 57263454, compound

Product 1

HCID 57060556HCID 57060556, compoundYield 118.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a solution of tert-butyl 4-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)piperidine-1-carboxylate (1.631 g) [see Preparation 31] in dichloromethane (10 ml) at 0° C. The reaction mixture was then warmed to room temperature and stirred for 2 hours, after which time the solvent was removed under reduced pressure and the residue was dissolved in water. Sodium hydrogen carbonate was added until the solution reached a pH of 8 and the product was then extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-(4-piperidinyl)-2-piperidinecarboxamide (1.48 g) as a white foam.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. additionSodium hydrogen carbonate was added until the solution
  4. extractionthe product was then extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e384a6c051f2459b917dcfe57c0b7560
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

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