Sodium Hydroxide → 2-Tert-butoxycarbonyloxyamino-thiazole-5-carboxylic acid

HRID 9096

Reaktionsgleichung

Reaktionsgleichung von HRID 9096
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:8][C:7]=1C)=[O:5])C.[OH-].[Na+]>O1CCCC1CO>[C:16]([O:15][C:13]([O:12][NH:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21911455Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

Produkt 1

HCID 219112552-Tert-butoxycarbonyloxyamino-thiazole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7360Tetrahydrofurfuryl alcoholLösungsmittel

Versuchsvorschrift

A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate (1.1 g, 4.2 mmol) in tetrahydrofuran-methanol (80 mL, 1:1) was treated with a 6N aq. NaOH solution (20 mL, 120 mmol). The mixture was stirred at rt for 24 h. Most of THF and methanol were removed by distillation under reduced pressure and the aq. Solution was acidified with 6 N aq. HCl solution (22 mL). The precipitated solid was filtered, washed with water and ether, air dried followed by drying in vacuo to obtain the title acid (940 mg, 96%) as an off-white solid.

Aufarbeitung

  1. customMost of THF and methanol were removed by distillation under reduced pressure
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water and ether, air
  4. customdried
  5. customby drying in vacuo
  6. customto obtain the title acid (940 mg, 96%) as an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-f30f6fee1bf24541893678b7a7c2463b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091223B2

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