Reaktion #604088

Reaktionsgleichung

triethylamine

(R)-2-Amino-3-methyl-butan-1-ol

Intermediate H

(R)-2-Amino-3-methyl-butan-1-ol

6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

Intermediate A

6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

→

6-Chloro-2-hydroxy-N-methoxy-3-[2-((R)-1-methoxymethyl-2-methyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-N-methyl-benzenesulfonamide

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONdissolved in EtOAc
3. 3
   WaschenThe EtOAc solution was washed with 1M HCl(aq) and NaHCO3 (aq)
4. 4
   ExtraktionThe NaHCO3 (aq) layer was extracted with EtOAc
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified
7. 7
   Sonstigeto furnish a brown solid [M+H]+ 462.0

Vorschrift

To a stirred solution of triethylamine (1.192 ml, 8.55 mmol) and (R)-2-Amino-3-methyl-butan-1-ol (Intermediate H) in EtOH (36 ml) was added 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide (Intermediate A) (1.67 g, 4.27 mmol). The reaction mixture was heated at 85° C. for 18 hours. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl(aq) and NaHCO3 (aq). The NaHCO3 (aq) layer was extracted with EtOAc. The EtOAc layers were combined and concentrated in vacuo. The residue was purified using flash chromatography (0-10% MeOH in DCM) to furnish a brown solid [M+H]+ 462.0.

Quelle