Propane sultone → 3-{[(1S)-2-ethoxy-1-methyl-2-oxoethyl]amino}-1-propanesulfonic acid

HRID 239766

Reaktionsgleichung

Reaktionsgleichung von HRID 239766
[CH2:1]([O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6])[CH3:2].[CH2:9]1[CH2:15][S:12](=[O:14])(=[O:13])[O:11][CH2:10]1>O1CCCC1>[CH2:1]([O:3][C:4](=[O:8])[C@@H:5]([NH:6][CH2:10][CH2:9][CH2:15][S:12]([OH:14])(=[O:13])=[O:11])[CH3:7])[CH3:2]

Komponenten

4

Edukt 2

HCID 14264Propane sultoneHCID 76507L-Alanine ethyl ester

Produkt 1

HCID 589318203-{[(1S)-2-ethoxy-1-methyl-2-oxoethyl]amino}-1-propanesulfonic acidAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of L-alanine ethyl ester (1.67 g, 14.3 mmol) in tetrahydrofuran (25 mL) was slowly added 1,3-propanesultone (1.42 g, 11.9 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL) and dried in vacuo, affording the title compound (1.19 g, 42%). 1H NMR (D2O, 500 MHz) δ ppm 4.16 (m, 2H), 4.01 (m, 1H), 3.12 (m, 2H), 2.87 (t, 2H, J=7.3 Hz), 2.01 (m, 2H), 1.43 (d, 3H, J=7.3 Hz), 1.14 (t, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) δ ppm 170.22, 63.84, 55.69, 47.94, 44.73, 21.51, 14.05, 13.25. [α]D=−2.4° (c=0.0022 in water), ES-MS 240 (M+1).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6c7a785fd3a42b5b4794fe61553ad67
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642801B2

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