Lithium hydroxide, monohydrate → N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine

HRID 275626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275626
C[O:2][C:3](=[O:41])[CH:4]([CH2:35][C:36]1[N:37]=[CH:38][S:39][CH:40]=1)[NH:5][C:6](=[O:34])[C@@H:7]([CH2:15][S:16]([C:19]([CH3:33])([C:21](=[O:32])[N:22]([CH3:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20])(=[O:18])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:33][C:19]([S:16]([CH2:15][C@@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]([NH:5][CH:4]([C:3]([OH:41])=[O:2])[CH2:35][C:36]1[N:37]=[CH:38][S:39][CH:40]=1)=[O:34])(=[O:18])=[O:17])([C:21](=[O:32])[N:22]([CH3:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 54195495N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine methyl ester

Produkt 1

HCID 18659451N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanineAusbeute 124,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 300 mg of N-[(S)-α-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine methyl ester in 2.5 ml of dioxan was treated with a solution of 24.3 mg of lithium hydroxide hydrate in 1 ml of water and stirred at 50 for 3 hours. Subsequently, the solution was partitioned between ethyl acetate and water and the organic phase was extracted three times with water. The aqueous extracts were adjusted to pH 2 with ethyl acetate and with 2N hydrochloric acid and evaporated under reduced pressure. There were obtained 365 mg of N-[(S)-α-[[[1 -methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D ,L-alanine as a colourless foam which was used directly in the next step.

Aufarbeitung

  1. customSubsequently, the solution was partitioned between ethyl acetate and water
  2. extractionthe organic phase was extracted three times with water
  3. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e57d4348d3e94caba79d3cc533542fc7
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393875

Notizen zur Reaktion

Wird geladen…