Reaction #51777

ord-7ad3e437a0294e5ab25fa470060edb17

Reaction equation

CC(C)(C)c1cc2[nH]c(=O)c(=O)[nH]c2cc1S
6-tert-butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione
Cc1ccc(S(=O)(=O)Br)cc1
tosyl bromide
c1ccncc1
pyridine
→
Cc1ccc(S(=O)(=O)Sc2cc3[nH]c(=O)c(=O)[nH]c3cc2C(C)(C)C)cc1
title compound
Cc1ccc(S(=O)(=O)Sc2cc3[nH]c(=O)c(=O)[nH]c3cc2C(C)(C)C)cc1
Toluene-4-thiosulfonic acid S-(7-tert-butyl-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-6-yl)ester

Reactants

CC(C)(C)c1cc2[nH]c(=O)c(=O)[nH]c2cc1S
6-tert-butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione
Cc1ccc(S(=O)(=O)Br)cc1
tosyl bromide
c1ccncc1
pyridine

Reagents

None

Solvents

CCOC(C)=O
EtOAc

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe crude product was purified by flash silica gel chromatography (5%-10% MeOH in CH2Cl2) as eluents

Procedure

The title compound was prepared according to the General Method 15 using 6-tert-butyl-7-mercapto-1,4-dihydro-quinoxaline-2,3-dione (prepared in Example DDD, 9.1 mmol), tosyl bromide (2.1 g, 9.1 mmol), pyridine (2 mL), EtOAc (50 mL). The crude product was purified by flash silica gel chromatography (5%-10% MeOH in CH2Cl2) as eluents. MS(APCI): 405 (M+H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06852711B2uspto-grants-2005_02