Lithium hydroxide, monohydrate → 3-[(4-Methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-3-ylmethyl)-amino]-5-phenyl-thiophene-2-carboxylic acid

HRID 73154

반응식

HRID 73154 반응식
C[O:2][C:3]([C:5]1[S:6][C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:8][C:9]=1[N:10]([C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH3:27])[CH2:23][CH2:22]1)=[O:20])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13]1)=[O:4].O[Li].O>C1COCC1.CO.O>[CH3:27][CH:24]1[CH2:25][CH2:26][CH:21]([C:19]([N:10]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13]2)[C:9]2[CH:8]=[C:7]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])=[O:20])[CH2:22][CH2:23]1

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 684249123-[(4-Methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-3-ylmethyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 104807573-[(4-Methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-3-ylmethyl)-amino]-5-phenyl-thiophene-2-carboxylic acid수율 118.9%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
55 °C

실험 절차

3-[(4-Methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-3-ylmethyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (162 mg, 0.27 mmol) was dissolved in a mixture of THF:MeOH:H2O (3:2:1, 2.8 mL) and treated with LiOH.H2O (35 mg, 0.81 mmol). The solution was heated at 55° C. for 3 h. The solvents were removed and the residue was acidified using HCl to pH 4. The product was extracted with EtOAc and the organic layers were washed with brine, dried and evaporated to provide 3-[(4-Methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-3-ylmethyl)-amino]-5-phenyl-thiophene-2-carboxylic acid (146 mg, 92% yield). 1H NMR (CDCl3, 400 MHz): 9.98 (br s, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.48-7.24 (m, 9H), 5.20-5.05 (m, 2H), 4.35-3.95 (m, 3H), 3.00 (m, 1H), 2.85-2.52 (m, 2H), 2.15 (m, 1H), 1.82-1.18 (m, 12H), 0.78 (d, 3H), 0.68 (m, 2H).

후처리

  1. customThe solvents were removed
  2. extractionThe product was extracted with EtOAc
  3. washthe organic layers were washed with brine
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-23d27e5dc69a44d9a30cb2d0d0ad2d70
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829030B2

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