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

HRID 516906

Reaktionsgleichung

Reaktionsgleichung von HRID 516906
[CH2:1](N(CC)CC)C.[NH2:8][C@H:9]([CH:12]([CH3:14])[CH3:13])[CH2:10][OH:11].[Cl:15][C:16]1[C:21]([S:22]([N:25]([O:27][CH3:28])[CH3:26])(=[O:24])=[O:23])=[C:20]([OH:29])[C:19]([NH:30][C:31]2[C:34](=O)[C:33](=[O:36])[C:32]=2[O:37]CC)=[CH:18][CH:17]=1>CCO>[Cl:15][C:16]1[C:21]([S:22]([N:25]([O:27][CH3:28])[CH3:26])(=[O:23])=[O:24])=[C:20]([OH:29])[C:19]([NH:30][C:31]2[C:32](=[O:37])[C:33](=[O:36])[C:34]=2[NH:8][C@@H:9]([CH2:10][O:11][CH3:1])[CH:12]([CH3:14])[CH3:13])=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6950587D-Valinol2×HCID 568442936-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide2×

Produkt 1

HCID 446291496-Chloro-2-hydroxy-N-methoxy-3-[2-((R)-1-methoxymethyl-2-methyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-N-methyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with 1M HCl(aq) and NaHCO3 (aq)
  4. extractionThe NaHCO3 (aq) layer was extracted with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. customto furnish a brown solid [M+H]+ 462.0

Quellen und Nachweise

ORD-Eintrag
ord-a0d44ceef7004143a68b7e6c54feefb1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115087B2

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