Lithium hydroxide, monohydrate → QX28Nxx8UG

HRID 23795노트

반응식

HRID 23795 반응식
C([O:3][C:4](=[O:37])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][C:34]([OH:36])=[O:35])[CH:27]=2)[S:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])C.O[Li].O>C1COCC1.O>[C:34]([CH2:33][O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][N:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:37])=[O:3])=[CH:9][CH:10]=1)[S:16]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])([OH:36])=[O:35]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrate2회HCID 697316782-(4-{[(3-Carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic Acid Ethyl Ester

생성물 1

HCID 10174435QX28Nxx8UG수율 94.5%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(4-{[(3-carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid ethyl ester (83 mg, 0.157 mmol) in THF (10 mL) was added water (1 mL) and LiOH.H2O (66 mg, 1.58 mmol). The reaction was heated at reflux for 24 h. Additional LiOH.H2O (66 mg, 1.58 mmol) in water (2 mL) was added and the reaction was heated at reflux for 30 h. The mixture was concentrated in vacuo and to the residue was added THF (3 mL) and water (1.5 mL). The reaction was heated at reflux for 24 h and was cooled to room temperature. The solution was diluted with water and the pH was adjusted to about 5 by addition of 1N HCl. Sodium chloride was added and the aqueous solution was washed with EtOAc (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated to provide the title compound (74 mg). 1H NMR (400 MHz, CDCl3) δ 8.94 (s, 1H), 8.73 (s, 1H), 8.13 (d, 1H), 7.55 (m, 1H), 7.23 (d, 2H), 7.11 (m, 3H), 6.78 (d, 1H), 6.73 (d, 1H), 6.68 (s, 1H), 4.90 (s, 2H), 4.39 (s, 2H), 3.30 (s, 2H), 1.50 (s, 6H); MS 497 (M−1).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 h
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 30 h
  5. concentrationThe mixture was concentrated in vacuo and to the residue
  6. additionwas added THF (3 mL) and water (1.5 mL)
  7. temperatureThe reaction was heated
  8. temperatureat reflux for 24 h
  9. additionThe solution was diluted with water
  10. additionthe pH was adjusted to about 5 by addition of 1N HCl
  11. additionSodium chloride was added
  12. washthe aqueous solution was washed with EtOAc (3×)
  13. dry with materialThe combined organic solutions were dried (MgSO4)
  14. filtrationfiltered
  15. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8d37fafa44e7460d90f98534c4ded948
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852863B2

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