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 545476노트

반응식

HRID 545476 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-c6ef1dc8ad1a4d78b0025c3191409550
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935724B2

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