Trifluoroacetic acid → HCID 131719118, compound

HRID 2399238Notes

Reaction equation

HRID 2399238 reaction equation
C(O)(C(F)(F)F)=O.[N:8]1(C(OC(C)(C)C)=O)[CH2:33][CH2:32][CH2:31][C@@H:9]1[C:10]([NH:12][C@@H:13]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11]>ClCCl>[NH:8]1[CH2:33][CH2:32][CH2:31][C@@H:9]1[C:10]([NH:12][C@@H:13]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131719117HCID 131719117, compound

Product 1

HCID 131719118HCID 131719118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Distilled TFA (4.60 ml, 59.6 mmol) was added dropwise to a solution of N-Boc-D-Pro-D-Phe-OBn (2.70 g, 5.96 mmol) in dry dichloromethane (5.0 ml), and the mixture was stirred at room temperature for 4 hours. TFA and solvent were then removed by evaporation under reduced pressure, and the resulting residue redissolved in chloroform. Water and solid potassium carbonate were added in amounts sufficient to achieve & pH of 10 in the resulting aqueous solution, and the aqueous layer was then extensively extracted with chloroform. The combined organic layers were dried over MgSO4 and concentrated to yield crude D-Pro-D-Phe-OBn as a yellow oil which was used without further purification.

Workup

  1. customTFA and solvent were then removed by evaporation under reduced pressure
  2. dissolutionthe resulting residue redissolved in chloroform
  3. additionWater and solid potassium carbonate were added in amounts sufficient
  4. extractionpH of 10 in the resulting aqueous solution, and the aqueous layer was then extensively extracted with chloroform
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f986a205db314a529f020285fec21ff0
Source dataset
uspto-grants-1995_09
Patent number
US05447915

Reaction notes

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