Sodium Hydroxide → 4-Methyl-2-(2-phenylthiazol-4-yl)pentanoic acid

HRID 1060741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060741
[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:10]1[N:11]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:13][CH:14]=1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:10]1[N:11]=[C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[S:13][CH:14]=1)[C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 18628735Ethyl 4-methyl-2-(2-phenylthiazol-4-yl)pentanoate

Produkt 1

HCID 110766664-Methyl-2-(2-phenylthiazol-4-yl)pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution comprised of the ethyl 4-methyl-2-(2-phenylthiazol-4-yl)pentanoate in methanol (5 mL) was treated with sodium hydroxide (0.1 gm, 2 mmol). The mixture was stirred for 4 hours, basified with 0.1 M sodium hydroxide solution, washed with ethyl acetate (10 mL), acidified and extracted with ethyl acetate (50 mL). The extract was washed with water, dried (MgSO4) and concentrated. Product was purified from the residue by flash chromatography on silica gel (60° A) with 33% ethyl acetate in hexane as an eluent to provide 4-methyl-2-(2-phenylthiazol-4-yl)pentanoic acid (200 mg, 1.44 mmol). Rf 0.41. 1H NMR (DMSO-d6): 1.01 (m, 6H), 1.61-1.79 (m, 3H), 3.63 (m, 1H), 7.04 (d, 1H), 7.22-7.34 (m, 5H). LCMS: 276.1 (M+H+).

Aufarbeitung

  1. washwashed with ethyl acetate (10 mL)
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customProduct was purified from the residue by flash chromatography on silica gel (60° A) with 33% ethyl acetate in hexane as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-aa95c1d0df4d472289e746f25d40dd93
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525036B2

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