Water → 2-(3,3-Dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid

HRID 1394105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394105
O.[CH3:2][C:3]([CH3:23])([CH3:22])[CH2:4][C:5]([NH:7][C:8]1[S:9][C:10]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O:19]CC)=[O:18])[C:11]=2[N:12]=1)=[O:6].[OH-].[Na+]>CO>[CH3:2][C:3]([CH3:23])([CH3:22])[CH2:4][C:5]([NH:7][C:8]1[S:9][C:10]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([OH:19])=[O:18])[C:11]=2[N:12]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 59681875Ethyl 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate

Produkt 1

HCID 596818712-(3,3-Dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Water (2 mL) and methanol (8 mL) were added to ethyl 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate (185 mg, 0.57 mmol) and NaOH (27 mg, 0.675 mmol), and the resultant mixture was stirred at room temperature under a blanket of nitrogen as inert gas. To complete the reaction, NaOH (200 mg, 5 mmol) was again added, and stirring was continued for a further 24 hours at room temperature. Following removal of MeOH, 2M HCl (10 mL) was added, and the resultant mixture was extracted with CH2Cl2 (3×20 mL). Following drying of the combined organic phases over Na2SO4 and filtration, there was obtained the product 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid in a yield of 144 mg (corresponding to 85% of theory).

Aufarbeitung

  1. additionwas again added
  2. customremoval of MeOH, 2M HCl (10 mL)
  3. additionwas added
  4. extractionthe resultant mixture was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialFollowing drying of the combined organic phases over Na2SO4 and filtration

Quellen und Nachweise

ORD-Eintrag
ord-d533b77ecbd0410d87b950828b8778cf
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348347B2

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