Reaction #3352

ord-1e43db34740c4500b323da3d86603bf8

Reaction equation

CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
2-([2-[3-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-pyridin-2-yldisulfanyl]pyridine-3-carbonyl]-amino)-4-methyl-pentanoic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O
title compound
Yield 77.4%
CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)O)C(=O)O
2-[[2-[3-(1-Carboxy-3-methylbutylcarbamoyl)-pyridin-2-yl-disulfanyl]-pyridine-3-carbonyl]-amino]-4-methyl-pentanoic acid
Yield 77.4%

Reactants

CC(C)CC(NC(=O)c1cccnc1SSc1ncccc1C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
2-([2-[3-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-pyridin-2-yldisulfanyl]pyridine-3-carbonyl]-amino)-4-methyl-pentanoic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagents

None

Solvents

COc1ccccc1
anisole
ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe general method of Preparation 20
  2. 2
    OtherThe crude product was recrystallized from methanol/water

Procedure

The general method of Preparation 20 was followed using [S-(R*,R*)]-2-([2-[3-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-pyridin-2-yldisulfanyl]pyridine-3-carbonyl]-amino)-4-methyl-pentanoic acid tert-butyl ester (1.9 g, 2.9 mmol) in 20 mL dichloromethane, anisole (1.5 mL), and 10 mL trifluoroacetic acid. The crude product was recrystallized from methanol/water to yield 1.2 g of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733921uspto-grants-1998_03