Hydrogen Bromide → HCID 18648268, Verbindung

HRID 742867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742867
C(OC([NH:11][C@@H:12]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:13]([OH:27])[CH2:14][N:15]1[C@H:19]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][S:17][CH2:16]1)=O)C1C=CC=CC=1.[BrH:35]>C(O)(=O)C.C(OCC)C>[BrH:35].[BrH:35].[NH2:11][C@@H:12]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C@H:13]([OH:27])[CH2:14][N:15]1[C@H:19]([C:20]([NH:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH2:18][S:17][CH2:16]1

Komponenten

5

Edukt 2

HCID 260Hydrogen BromideHCID 573244103-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide

Produkt 1

HCID 18648268HCID 18648268, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 2 g of 3-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide and 4.1 ml of 32% (w/w) hydrogen bromide in glacial acetic acid was stirred at room temperature for 1 hour. The resulting solution was diluted with anhydrous diethyl ether and the precipitated product was rapidly filtered off and washed with fresh diethyl ether. There were obtained 2.01 g of 3-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide dihydrobromide as a white solid: 1H NMR (300 MHz): δ (D2O) 1.37 (9H, s), 3.0 (2H, m), 3.09 (2H, dq), 3.29 (2H, d), 3.85 (2H, m), 4.16 (1H, m), 4.3 (2H, q) and 7.42 (5H, m) ppm.

Aufarbeitung

  1. filtrationthe precipitated product was rapidly filtered off
  2. washwashed with fresh diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0d875a9ac43c4267ac19dd199959c0ea
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554756

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