Trifluoroacetic acid → L-Pro-L-Phe-OBn

HRID 1356856Notes

Reaction equation

HRID 1356856 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[NH2:16][C@H:17]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.N1(C(OC(C)(C)C)=O)CCC[C@H]1C(N[C@H](C(OCC1C=CC=CC=1)=O)CC1C=CC=CC=1)=O.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>CN(C=O)C>[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:16][C@H:17]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:5]

Participants

9

Reactant 7

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 79724-MethylmorpholineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 736312Benzyl 3-phenyl-L-alaninateHCID 131723154Boc-L-Pro-L-Phe-OBn

Product 1

HCID 53647100L-Pro-L-Phe-OBn

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-L-Pro-OH and L-Phe-OBn.Hcl were treated with BOP and NMM in DMF to give, after aqueous workup and flash chromatography, Boc-L-Pro-L-Phe-OBn. This product was then treated with TFA and anisole, and the mixture was evaporated. The residue was dissolved in Et2O and washed with saturated aqueuos NaHCO3 and saturated aqueous NaCl. The Et2O layer was dried over anhydrous MgSO4, filtered, and the solvent evaporated to give L-Pro-L-Phe-OBn. The residue was treated with CH3SO2Cl and Et3N in CH2Cl2 to give, after aqueous workup and flash chromatography, N-(CH3SO2)-L-Pro-L-Phe-OBn. This product was then treated with 10% Pd on C in THF, and the mixture was shaken under 50 psi H2. The mixture was filtered through Celite, and evaporated to give the title compound as a clear oil.

Workup

  1. customto give
  2. customthe mixture was evaporated
  3. dissolutionThe residue was dissolved in Et2O
  4. washwashed with saturated aqueuos NaHCO3 and saturated aqueous NaCl
  5. dry with materialThe Et2O layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-1769f7c04a1141b2896906b9c76b886f
Source dataset
uspto-grants-2003_07
Patent number
US06586602B2

Reaction notes

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