Lithium Hydroxide → (3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid

HRID 968518

Reaktionsgleichung

Reaktionsgleichung von HRID 968518
C[O:2][C:3]([C@@H:5]1[CH2:10][S:9][CH2:8][CH2:7][N:6]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])=[O:4].[Li+].[OH-].C(OCC)(=O)C>CO>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([S:11]([N:6]2[CH2:7][CH2:8][S:9][CH2:10][C@H:5]2[C:3]([OH:4])=[O:2])(=[O:13])=[O:12])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 69416803(3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid methyl ester

Produkt 1

HCID 69415969(3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acidAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

8.3 g of (3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid methyl ester was dissolved in 157 mL of methanol and 52.5 ml 1 mol/L of LiOH solution was added dropwise in the above solution at 0° C. The mixture was stirred for 48 h and ethyl acetate (60, 60 ml) was added into the reaction mixture and separated to collect mother liquid. The mother liquid was acidified by 100 ml 1 mol/L hydrogen chloride to adjust pH value to 2. Filtrated and collected the white solid to obtain 7.7 g product. Yield 97.0%□mp149-150° C.

Aufarbeitung

  1. customseparated
  2. customto collect mother liquid
  3. filtrationFiltrated
  4. customcollected the white solid

Quellen und Nachweise

ORD-Eintrag
ord-df3cdd5c4a114f0b8cca63a0c2f282a8
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304057B2

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