Trifluoroacetic acid → HCID 131719809, compound

HRID 1857682Notes

Reaction equation

HRID 1857682 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>C(Cl)Cl>[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 6344DichloromethaneSolvent

Procedure

The resultant Boc-Hyp-Pal-N(Me)Bzl-is dissolved in 40 ml of CH2Cl2 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-6c4f29aed0ad447fac3677abacbe348a
Source dataset
uspto-grants-2000_11
Patent number
US06147212

Reaction notes

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