Trifluoroacetic acid → HCID 20824389, compound

HRID 1243524Notes

Reaction equation

HRID 1243524 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:15][CH2:14]1)=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:15][CH2:14]1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21927935HCID 21927935, compound

Product 1

HCID 20824389HCID 20824389, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 4-{4-[N-(tert-butoxycarbonyl)-beta-alanyl]piperazin-1-yl}-butanoate (290 mg, 0.8 mmoles) in 2 mL dichloromethane was added 2 mL trifluoroacetic acid. After 1 hour the solvents were evaporated. The residue was dissolved in 10% DMF/DCM and MP-carbonate (0.8 g) was added. After 16 h the solution was filtered and evaporated to afford methyl 4-(4-beta-alanylpiperazin-1-yl)butanoate (87 mg, 41%) as an oil. MS (ESI+) for m/z 272 (M+H)+.

Workup

  1. customAfter 1 hour the solvents were evaporated
  2. dissolutionThe residue was dissolved in 10% DMF/DCM
  3. additionMP-carbonate (0.8 g) was added
  4. filtrationAfter 16 h the solution was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-a854cf5a183c48ae970e150a6201ccaa
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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