Reaction #3351

ord-30c9c4c43e504a87b22ef5a3d62b32e8

Reaction equation

Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1
2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5-methyl-phenyldisulfanyl]-4-methyl-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
→
Cc1cccc([SH](Sc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(CC(C)C)C(=O)O)c1
title compound
Cc1cccc([SH](Sc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(CC(C)C)C(=O)O)c1
2-[2-[-(1-Carboxy-3-methyl-butylcarbamoyl)-5-methylphenyldisulfanyl]-4-methylbenzoylamino]-4-methyl-pentanoic acid

Reactants

Cc1ccc(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(SSc2cc(C)ccc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1
2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5-methyl-phenyldisulfanyl]-4-methyl-benzoylamino]-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-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-5-methyl-phenyldisulfanyl]-4-methyl-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester (1.9 g, 2.8 mmol) in 20 mL dichloromethane, anisole (2.0 mL), and 10 mL trifluoroacetic acid. The crude product was recrystallized from methanol/water to yield 1.1 g of the title compound.

Source

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