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 545476Notes

Reaction equation

HRID 545476 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-c6ef1dc8ad1a4d78b0025c3191409550
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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