Trifluoroacetic acid → HCID 86757994, compound

HRID 843748Notes

Reaction equation

HRID 843748 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][C@@H:8]([C:35]#[N:36])[NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:34])[CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH2:13]1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:24]1[CH2:25][CH2:26][CH:21]([CH2:20][CH2:19][C:18]([N:14]2[CH2:15][CH2:16][CH2:17][C@@H:12]([C:10]([NH:9][C@H:8]([C:35]#[N:36])[CH2:7][C:6]([OH:37])=[O:5])=[O:11])[CH2:13]2)=[O:34])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757995HCID 86757995, compound

Product 1

HCID 86757994HCID 86757994, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-cyano-β-alanine tert-butyl ester (460.9 mg) in dichloromethane (5 ml) was added trifluoroacetic acid (4.6 ml). After stirring at ambient temperature for 2 hours, the mixture was concentrated in vacuo. The residue was dissolved in water and desalted by HP-20 eluting with (IPA:water=1:1). The eluting solution was concentrated in vacuo and freeze-dried to give N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-cyano-β-alanine (0.12 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. washeluting with (IPA:water=1:1)
  4. concentrationThe eluting solution was concentrated in vacuo
  5. customfreeze-dried

Sources & evidence

ORD record
ord-df91f4e4d4f24985b924f5eef93dc97a
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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