Heptane → methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate

HRID 742064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742064
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH3:24]CCCCCC>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@H:13]([CH:14]([CH3:16])[CH3:15])[C:17]([O:19][CH3:24])=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 8900HeptaneHCID 24386Thionyl ChlorideHCID 1133588N-[4-methoxybenzenesulfonyl]-(D)-valine

Produkt 1

HCID 10946547methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of N-[4-methoxybenzenesulfonyl]-(D)-valine (8369 g, 29.13 mol) in methanol (30 L) at 5° C. is added thionyl chloride (2176 mL, 29.7 mol) over 2.5 hours. After stirring for 3 hours at 5° C., the reaction is stirred for 36 hours at room temperature. Most of the solvent is evaporated, and the crude product is dissolved in toluene (80 L). The toluene layer is then washed with water (20 L), saturated sodium bicarbonate (20 L), water again (20 L), 2N hydrochloric acid (20 L), brine (20 L), dried (Na2SO4), and the solvent is evaporated. The solid obtained is dissolved in ethyl acetate (8 L) and heptane (16 L) is added to induce crystallization. The precipitated product is collected by filtration to provide methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate.

Aufarbeitung

  1. stirringthe reaction is stirred for 36 hours at room temperature
  2. customMost of the solvent is evaporated
  3. dissolutionthe crude product is dissolved in toluene (80 L)
  4. washThe toluene layer is then washed with water (20 L), saturated sodium bicarbonate (20 L), water again (20 L), 2N hydrochloric acid (20 L), brine (20 L)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe solid obtained
  8. customcrystallization
  9. filtrationThe precipitated product is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-50f2adec32c14d05959b81a4942581fc
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552419

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