Thionyl Chloride → (5S)-4,5-Dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]oxathiazole-2-oxide

HRID 566592

Reaktionsgleichung

Reaktionsgleichung von HRID 566592
[S:1](Cl)(Cl)=[O:2].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH2:12][C@@H:13]([OH:15])[CH3:14].C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:14][C@@H:13]1[O:15][S:1](=[O:2])[N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=2)[CH2:12]1

Komponenten

6

Edukt 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 820205(S)-N-(2-pyridyl)-1-amino-2-propanol

Produkt 1

HCID 21339419(5S)-4,5-Dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]oxathiazole-2-oxideAusbeute 115,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Thionyl chloride (8.8 ml, 14.35 g 0.12M) in dichloromethane (20 ml) was added dropwise to a cooled stirred solution of (S)-N-(2-pyridinyl)-1-amino-2-propanol (18.28 g, 0.12M) in dichloromethane (180 ml) and diisopropylethylamine (31 g, 0.24M) keeping the temperature below 5° C. After stirring at 0° for 1 h a solution of saturated sodium bicarbonate solution was added keeping the temperature below 5° C. The organic layer was separated, dried (Na2SO4) and concentrated to give 27.6 g of a yellow oil. The oil was chromatographed on silica using 40% ethyl acetate in hexane to give 20.28 g of a yellow oil containing a 4:3 mixture of diastereoisomers.

Aufarbeitung

  1. customthe temperature below 5° C
  2. additionwas added
  3. customthe temperature below 5° C
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7ee4add36fd5477a9cb79d5f8e2644de
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06175012B1

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