Hydrochloric Acid → (R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol

HRID 1879338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879338
C([O:3][C:4](=O)[C@@H:5]([NH2:18])[C@@H:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[OH:7])C.[BH4-].[K+].Cl.O>CO>[NH2:18][C@H:5]([CH2:4][OH:3])[C@@H:6]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1)[OH:7]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4192641Potassium borohydrideHCID 34175685(2S,3R)-Ethyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate

Produkt 1

HCID 6452441(R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(2S,3R)-Ethyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate (Compound VIc) (10 g, 0.0348 moles) in methanol (about 100 mL) is reacted in a reaction vessel with potassium borohydride (about 2.8 g, 0.0522 moles) over about 6 hours while maintaining the temperature below about 60° C. The reaction is cooled to ambient room temperature and about 1N HCl and water (about 75 mL) are added. Thereafter, the solution is heated to evaporate the methanol. Next, sodium hydroxide is added (about 25%), the resulting solids are filtered and washed with water, then dried to yield (1R,2R)-2-amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol (Compound V wherein R1 is methylsulfonyl).

Aufarbeitung

  1. temperaturewhile maintaining the temperature below about 60° C
  2. temperatureThereafter, the solution is heated
  3. customto evaporate the methanol
  4. additionNext, sodium hydroxide is added (about 25%)
  5. filtrationthe resulting solids are filtered
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-311253c4149e445aa90e865a3291f6be
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314252B2

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