Trifluoroacetic acid → (L-Leucyl)glycine benzyl ester

HRID 1195128Notes

Reaction equation

HRID 1195128 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[CH2:10][NH:11][C:12](=[O:26])[C@H:13]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:14]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[CH2:10][NH:11][C:12](=[O:26])[C@H:13]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH2:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13242213BOC-Leu-Gly-OBzl

Product 1

HCID 13242215(L-Leucyl)glycine benzyl esterYield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1.29 g of the ester from Example 20 (step A) in 3.5 ml of methylene chloride was treated with 3.5 ml of trifluoroacetic acid and the solution stirred 2.5 hours at ambient temperature. The solution was then concentrated under a stream of nitrogen and the residue dissolved in methylene chloride/diethyl ether. The solution was washed 2 times with saturated aqueous sodium carbonate solution and the organic phase was then dried with sodium sulfate and filtered. Concentration under vacuum provided 919 mg of the title compound as a yellow oil.

Workup

  1. concentrationThe solution was then concentrated under a stream of nitrogen
  2. dissolutionthe residue dissolved in methylene chloride/diethyl ether
  3. washThe solution was washed 2 times with saturated aqueous sodium carbonate solution
  4. dry with materialthe organic phase was then dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-1225e96bef60457c8640daaf12c8d59d
Source dataset
uspto-grants-1992_05
Patent number
US05110799

Reaction notes

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