Reaction #315259

Reaction equation

methyl 2-{4-[(2R)-2-({(3S)-2-[(tert-butyl)oxycarbonyl](3-1,2,3,4-tetrahydroisoquinolyl)}carbonylamino)-3-(4-chlorophenyl)propanoyl]piperazinyl}benzoate

LiOH

→

title compound

Yield 61.8%

2-{4-[(2R)-2-({(3S)-2-[(Tert-Butyl)Oxycarbonyl](3-1,2,3,4-Tetrahydroisoquinolyl)}Carbonylamino)-3-(4-Chlorophenyl)Propanoyl]Piperazinyl}Benzoic Acid

Yield 61.8%

Solvents

THF

H2O

Conditions

Workup

1. 1
   OtherTo a 150 mL round-bottomed flask equipped
2. 2
   TemperatureAfter cooling to RT
3. 3
   Concentrationthe mixture was concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with EtOAc (100 mL)
5. 5
   workup.ADDITIONA 10% soln of citric acid (25 mL) was added
6. 6
   Otherthe organic layer was separated
7. 7
   Extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
8. 8
   Washwashed with H2O, and brine
9. 9
   Dryingdried over Na2SO4
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated in vacuo

Procedure

To a 150 mL round-bottomed flask equipped with magnetic stirring was added methyl 2-{4-[(2R)-2-({(3S)-2-[(tert-butyl)oxycarbonyl](3-1,2,3,4-tetrahydroisoquinolyl)}carbonylamino)-3-(4-chlorophenyl)propanoyl]piperazinyl}benzoate (1.6 g, 2.4 mmol) in THF (30 mL). A soln of LiOH (Aldrich) (303 mg, 7.14 mmol) in H2O (ca. 10 mL) was added and the reaction was heated at 60° C. for 12 h. After cooling to RT, the mixture was concentrated in vacuo and diluted with EtOAc (100 mL). A 10% soln of citric acid (25 mL) was added, the organic layer was separated, and the aqueous layer was extracted with EtOAc (2×25 mL). The organic layers were combined, washed with H2O, and brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a white solid (960 mg). MS (ESI, pos. ion) m/z: 647 (M+H). Calc'd for C35H39ClN4O6: 646.26.

Source