Acetic Acid → HCID 57419866, Verbindung

HRID 1810458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810458
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH2:14]([NH2:16])[CH3:15].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:14]([NH:16][CH2:4][C:3]1[CH:6]=[C:7]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1])[CH3:15]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 574198652-Hydroxy-5-(methanesulfonyl)benzaldehyde

Produkt 1

HCID 57419866HCID 57419866, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2-Hydroxy-5-methanesulfonyl-benzaldehyde (0.200 g, 1.0 mmol), ethylamine (2M in THF; 0.75 mL, 1.5 mmol), and sodium cyanoborohydride (0.095 g, 1.5 mmol) were combined in MeOH (10 mL). 4 Å Molecular sieves were added, followed by acetic acid (0.09 mL, 1.5 mmol), and the reaction was stirred for 1 hour. The mixture was filtered, and H2O (0.5 mL) was added and the solution was concentrated. The residue was partitioned between EtOAc (100 mL) and brine (20 mL), and the mixture was neutralized with 1N aqueous HCl (lint) and extracted six times with EtOAc, until minimal product was seen in the aqueous layer by analytical tlc. The combined organic layers were dried, filtered, and concentrated to give the title compound.

Aufarbeitung

  1. addition4 Å Molecular sieves were added
  2. filtrationThe mixture was filtered
  3. additionH2O (0.5 mL) was added
  4. concentrationthe solution was concentrated
  5. customThe residue was partitioned between EtOAc (100 mL) and brine (20 mL)
  6. extractionextracted six times with EtOAc
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-67e8cf584bb7425eafec5659e87e298a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362044B2

Notizen zur Reaktion

Wird geladen…