Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Anisole | HCID 7519 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | Benzyl 3-phenyl-L-alaninate | HCID 736312 | — |
| Reactant | Boc-L-Pro-L-Phe-OBn | HCID 131723154 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | L-Pro-L-Phe-OBn | HCID 53647100 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06586602B2 |
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| Source dataset | uspto-grants-2003_07 |
|---|
| ORD ID | ord-1769f7c04a1141b2896906b9c76b886f |
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| Source note | uspto-grants-2003_07 |
|---|
