Trifluoroacetic acid → HCID 131719809, compound

HRID 1458205Notes

Reaction equation

HRID 1458205 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:28][C@H:26]([OH:27])[CH2:25][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:17])=[O:15])[CH2:7][C:8]1[CH:13]=[N:12][CH:11]=[CH:10][CH:9]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCl>[NH:1]1[CH2:28][C@H:26]([OH:27])[CH2:25][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:17])=[O:15])[CH2:7][C:8]1[CH:13]=[N:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131719810HCID 131719810, compound

Product 1

HCID 131719809HCID 131719809, compound

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

The resultant Boc-Hyp-Pal-N(Me)Bzl is dissolved in 40 ml of CH2 Cl2 and mixed with 20 ml of TFA whilst cooling with ice. The mixture is stirred for 15 minutes at ambient temperature, concentrated on the rotary evaporator, the residue is taken up in ethyl acetate and extracted twice with saturated NaHCO3 solution. The aqueous phase is extracted successively with ethyl acetate and CH2Cl2. All the organic phases are united, dried with MgSO4, concentrated and the residue is chromatographed over silica gel by means of acetonitrile/water/MeOH (4:1:1). 0.39 g of H-Hyp-Pal-N(Me)Bzl is obtained as a highly viscous, colourless oil.

Workup

  1. temperaturewhilst cooling with ice
  2. concentrationconcentrated on the rotary evaporator
  3. extractionextracted twice with saturated NaHCO3 solution
  4. extractionThe aqueous phase is extracted successively with ethyl acetate and CH2Cl2
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customthe residue is chromatographed over silica gel by means of acetonitrile/water/MeOH (4:1:1)

Sources & evidence

ORD record
ord-51eb2331fbab40c6a1cbc0f677bc185e
Source dataset
uspto-grants-1998_12
Patent number
US05849918

Reaction notes

Loading…