Sodium Hydroxide → 4-Cyano-5-morpholin-4-ylthiophene-2-carboxylic acid

HRID 1615509노트

반응식

HRID 1615509 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16]CC)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].[OH-].[Na+]>C1COCC1.CO.O>[C:1]([C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 68629708Ethyl 4-cyano-5-morpholin-4-ylthiophene-2-carboxylate

생성물 1

HCID 686278674-Cyano-5-morpholin-4-ylthiophene-2-carboxylic acid수율 88%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

To a solution of ethyl 4-cyano-5-morpholin-4-ylthiophene-2-carboxylate (0.06 g, 0.23 mmol) in THF/MeOH/water (3:1:1) (5 mL) was added sodium hydroxide (0.095 g, 2.3 mmol). The reaction mixture was allowed to stir at rt for 20 h and was concentrated. The residue was acidified to pH 1-2 with 1N HCl and was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (0.048 g, 88%). LCMS: (FA) ES+ 239.1. 1H NMR (400 MHz, d6-DMSO) δ:7.67 (s, 1H), 3.72-3.75 (m, 4H) and 3.52-3.55 (m, 4H).

후처리

  1. concentrationwas concentrated
  2. extractionwas extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-27a96d5fc0e743fda9073848c0c33ed5
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765746B2

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