Trifluoroacetic acid → HCID 18727496, compound

HRID 720905Notes

Reaction equation

HRID 720905 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21](=[O:40])[CH2:22][N:23]([C:25]([CH:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)=[O:26])[CH3:24])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:14]1([CH2:13][CH2:12][CH2:11][CH:10]([NH:20][C:21](=[O:40])[CH2:22][N:23]([C:25]([CH:27]2[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]2)=[O:26])[CH3:24])[CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18727508HCID 18727508, compound

Product 1

HCID 18727496HCID 18727496, compoundYield 138%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(N-tert-Butoxycarbonyl-piperidine-4-carbonyl)-(N-methyl)-2-aminoacetic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (67) (1.46 g; 2.66 mmol) is dissolved in methylene chloride (30 mL) at ambient temperature. Trifluoroacetic acid (15 mL) is added in a slow stream, and the solution is stirred for 2 hours at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is dissolved in methylene chloride (200 mL) and poured onto saturated sodium bicarbonate solution. The pH is adjusted to 9 with saturated potassium carbonate solution. The mixture is shaken the layers separated. The water layer is extracted with methylene chloride (3×50 mL). The combined organic extracts are washed with water, dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (1.65 g) as a clear oil. ESMS:MH+ 450.2

Workup

  1. concentrationThe solution is concentrated in vacuo at 40° C
  2. dissolutionThe residue is dissolved in methylene chloride (200 mL)
  3. additionpoured onto saturated sodium bicarbonate solution
  4. stirringThe mixture is shaken the layers
  5. customseparated
  6. extractionThe water layer is extracted with methylene chloride (3×50 mL)
  7. washThe combined organic extracts are washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd412bb32ebd4ed79b93cbf4284fb9ab
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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