Lithium Hydroxide → (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

HRID 276299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 276299
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:14][S:13]2)=[C:7]([CH3:25])[CH:6]=1)=[O:4].[Li+].[OH-]>CO.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:14][S:13]2)=[C:7]([CH3:25])[CH:6]=1)([OH:4])=[O:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 56989530(4S)-2-(4-methoxycarbonyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

Produkt 1

HCID 57222223(4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (4S)-2-(4-methoxycarbonyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (prepared in a manner analogous to that described in Method D2a; 0.035 g, 0.097 mmol) in a mixture of MeOH (1.5 mL) and H2O (1.5 mL) was added LiOH (0.016 g, 0.39 mmol). The resulting mixture was stirred for 2 d at room temp., then was concentrated under reduced pressure. The residue was adjusted to pH 1 with a 1% HCl solution, then extracted with EtOAc (4×10 mL). The combined organic layers were sequentially washed with H2O (15 mL), a saturated NaCl solution (15 mL), and dried (Na2SO4). Concentration under reduced pressure gave (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (0.034 g, 100%): TLC (40% EtOAc/hex) Rf 0.08. This material was used in the next step without further purification.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted with EtOAc (4×10 mL)
  3. washThe combined organic layers were sequentially washed with H2O (15 mL)
  4. dry with materiala saturated NaCl solution (15 mL), and dried (Na2SO4)
  5. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-08191173ef1345d48ffc6d55a539a27c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

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