Reaction #1687137

ord-119e1b0ee94a472b9408dac9c44e1ea8

Reaction equation

CC(C)(C)OC(=O)[C@H](CNC(=O)c1ccc(CCc2ccc3c(n2)NCCC3)cc1)NS(=O)(=O)c1ccccc1
32-6
CC(C)(C)OC(=O)[C@H](CNC(=O)c1ccc(CCc2ccc3c(n2)NCCC3)cc1)NS(=O)(=O)c1ccccc1
4-[2-(1,2,3,4-Tetrahydro-1,8-naphthyridin-7-yl)ethyl]benzoyl-2(S)-phenylsulfonylamino-β-alanine t-butyl ester
O=C(O)C(F)(F)F
TFA
→
O=C(NC[C@H](NS(=O)(=O)c1ccccc1)C(=O)O)c1ccc(CCc2ccc3c(n2)NCCC3)cc1
32-7
O=C(NC[C@H](NS(=O)(=O)c1ccccc1)C(=O)O)c1ccc(CCc2ccc3c(n2)NCCC3)cc1
4-[2-(1,2,3,4-Tetrahydro-1,8-naphthyridin-7-yl)ethyl]benzoyl-2(S)-phenylsulfonylamino-β-alanine

Reactants

CC(C)(C)OC(=O)[C@H](CNC(=O)c1ccc(CCc2ccc3c(n2)NCCC3)cc1)NS(=O)(=O)c1ccccc1
32-6
CC(C)(C)OC(=O)[C@H](CNC(=O)c1ccc(CCc2ccc3c(n2)NCCC3)cc1)NS(=O)(=O)c1ccccc1
4-[2-(1,2,3,4-Tetrahydro-1,8-naphthyridin-7-yl)ethyl]benzoyl-2(S)-phenylsulfonylamino-β-alanine t-butyl ester
O=C(O)C(F)(F)F
TFA

Reagents

None

Solvents

ClCCl
CH2Cl2

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction was concentrated
  2. 2
    Otherthe solid residue purified by flash chromatography (silica, 19:1 EtOH/NH4OH)

Procedure

A solution of 32-6 (221 mg, 0.39 mmol), TFA (5 mL) and CH2Cl2 (50 mL) was stirred under ambient conditions for 18 h. The reaction was concentrated and the solid residue purified by flash chromatography (silica, 19:1 EtOH/NH4OH) to give 32-7 as a pale yellow solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05741796uspto-grants-1998_04