2-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester → 2-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid

HRID 545476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545476
C[O:2][C:3]([C:5]1[CH:23]=[CH:22][C:8]2[S:9][C:10]([C:12](=[O:21])[NH:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]>C1COCC1.[OH-].[Na+]>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]1[O:14][NH:13][C:12]([C:10]1[S:9][C:8]2[CH:22]=[CH:23][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH:11]=1)=[O:21]

Komponenten

4

Edukt 1

HCID 589689592-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester

Produkt 1

HCID 589690532-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 2-(tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester (131.6 mg, 0.39 mmol) in THF (2 mL) and 1M aqueous NaOH (4 mL) was allowed to stir at rt for 18 h. After removal of THF, the aqueous phase was acidified with HOAc to pH≈3. The solid formed was filtered, collected and dried to give 2-(tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid as a white solid. 1H NMR (DMSO-d6, 200 MHz) δ 12.04 (brs, 1H), 8.54 (s, 1H), 8.22-8.08 (m, 2H), 7.97 (dd, J=8.4, 1.2 Hz, 1H), 5.01 (s, 1H), 4.18-3.94 (m, 1H), 3.68-3.46 (m, 2H), 1.88-1.40 (m, 6H). MS (EI): cal'd 322.1 (MH+), exp 322.2 (MH+).

Aufarbeitung

  1. customAfter removal of THF
  2. customThe solid formed
  3. filtrationwas filtered
  4. customcollected
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c6ef1dc8ad1a4d78b0025c3191409550
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935724B2

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