Lithium hydroxide, monohydrate → (S)-4-methyl-2-[2-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-2,5-dihydro-pyrrol-1-yl]-pentanoic acid

HRID 19062노트

반응식

HRID 19062 반응식
C[O:2][C:3](=[O:26])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:25])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1.O>[CH3:7][CH:6]([CH3:8])[CH2:5][C@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:25])[C:3]([OH:26])=[O:2]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 66893856(S)-4-methyl-2-[2-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester

생성물 1

HCID 66894447(S)-4-methyl-2-[2-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-2,5-dihydro-pyrrol-1-yl]-pentanoic acid수율 68.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A mixture of (S)-4-methyl-2-[2-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester (94 mg, 0.26 mmol) in tetrahydrofuran (1.5 mL) and water (0.5 mL) was treated with lithium hydroxide monohydrate (14 mg, 0.33 mmol). The reaction was stirred at 25° C. for 3 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (25 mL) and was extracted with diethyl ether (1×25 mL). The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution and then extracted with 10% methanol/dichloromethane (2×25 mL). The organics were then dried over magnesium sulfate, filtered, rinsed with dichloromethane and concentrated in vacuo to afford (S)-4-methyl-2-[2-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-2,5-dihydro-pyrrol-1-yl]-pentanoic acid (61 mg, 67%) as an orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.87 (d, J=6.3 Hz, 3H), 0.93 (d, J=6.3 Hz, 3H), 1.36-1.84 (m, 7H), 2.53-2.61 (m, 2H), 2.68-2.83 (m, 2H), 4.12 (d, J=17.8 Hz, 1H), 4.24 (d, J=17.8 Hz, 1H), 4.62 (dd, J=11.2, 4.2 Hz, 1H), 4.66 (s, 1H), 6.99-7.07 (m, 2H), 7.18 (t, J=7.8 Hz, 1H), 12.84 (br. s., 1H).

후처리

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (25 mL)
  3. extractionwas extracted with diethyl ether (1×25 mL)
  4. extractionextracted with 10% methanol/dichloromethane (2×25 mL)
  5. dry with materialThe organics were then dried over magnesium sulfate
  6. filtrationfiltered
  7. washrinsed with dichloromethane
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1dc3d49f06d84845aba83b6437e50b0b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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