Glycine → [(7-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642331
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[C:9]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:17][C:8]=2[C:7]=1[OH:24])=[O:5])C.[NH2:25][CH2:26][C:27]([OH:29])=[O:28]>C[O-].[Na+].CO>[OH:24][C:7]1[C:8]2[S:17][C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:15][C:9]=2[C:10]([CH2:12][CH2:13][CH3:14])=[N:11][C:6]=1[C:4]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:5]

Komponenten

4

Edukt 2

HCID 750GlycineHCID 684281827-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Produkt 1

HCID 24757244[(7-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23694274Sodium methanolate methanolLösungsmittel

Versuchsvorschrift

A mixture of 7-hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (78 mg, 0.23 mmol) and glycine (343 mg, 4.57 mmol) in 0.5 M sodium methoxide/methanol (8.6 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (30 mL) and extracted three times with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (6 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (70 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.02 (br s, 1H), 9.21 (br s, 1H), 8.17 (m, 2H), 7.65 (m, 3H), 4.06 (d, J=6.2 Hz, 2H), 3.33 (m, 2H), 1.92 (m, 2H), 1.04 (t, J=7.0 Hz, 3H); MS: (+) m/z 371.93 (M+1).

Aufarbeitung

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (30 mL)
  4. extractionextracted three times with methyl t-butyl ether
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1a008bc6230942d283c7c8ed0ada0430
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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