Lithium Hydroxide → (S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetic acid

HRID 2416747Notes

Reaction equation

HRID 2416747 reaction equation
[Li+].[OH-].[CH3:3][NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][C:14]2[CH:38]=[CH:37][C:17]3[CH2:18][C@@H:19]([CH2:32][C:33]([O:35]C)=[O:34])[C:20](=[O:31])[N:21]([CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:22][C:16]=3[CH:15]=2)[CH:8]=[CH:7][CH:6]=1>C1COCC1.O>[CH3:3][NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][C:14]2[CH:38]=[CH:37][C:17]3[CH2:18][C@@H:19]([CH2:32][C:33]([OH:35])=[O:34])[C:20](=[O:31])[N:21]([CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:22][C:16]=3[CH:15]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57217922methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

Product 1

HCID 54052362(S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetic acidYield 55.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0N LiOH (0.62 mL, 0.62 mmole) was added to a solution of methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (250 mg, 0.51 mmole) in THF (2.5 mL) and H2O (1.9 mL) at 0°0 C., and the reaction was allowed to stir at RT for 18 hr. The mixture was washed with Et2O (2×5 mL) then a mild vacuum was applied to remove residual organic solvents. The aqueous layer was passed through a 0.45 μm Acrodisk filter then was carefully acidified to pH 6 using 10% HCl in H2O at 0° C. The precipitate was collected, washed with H2O, and dried under vacuum at 50° C. to give the title compound (134 mg, 55%) as a white solid: MS (ES) m/e 474 (M+H)+. Anal. Calcd for C28H31N3O4.0.75 H2O: C, 69.05; H, 6.73; N, 8.63. Found: C, 69.23; H, 6.59; N, 8.55.

Workup

  1. washThe mixture was washed with Et2O (2×5 mL)
  2. customto remove residual organic solvents
  3. filtrationfilter
  4. customat 0° C
  5. customThe precipitate was collected
  6. washwashed with H2O
  7. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-b56f3a418bc34b33973eb58158b81ed1
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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