Lithium hydroxide, monohydrate → [3-Oxo-8-[3-(pyridin-2-ylamino)-propoxy]-2-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-acetic acid

HRID 2416742Notes

Reaction equation

HRID 2416742 reaction equation
O[Li].O.[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:36]=[CH:35][C:18]2[CH2:19][C@H:20]([CH2:30][C:31]([O:33]C)=[O:32])[C:21](=[O:29])[N:22]([CH2:24][C:25]([F:28])([F:27])[F:26])[CH2:23][C:17]=2[CH:16]=1>C1COCC1.O>[O:29]=[C:21]1[C@@H:20]([CH2:30][C:31]([OH:33])=[O:32])[CH2:19][C:18]2[CH:35]=[CH:36][C:15]([O:14][CH2:13][CH2:12][CH2:11][NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][N:4]=3)=[CH:16][C:17]=2[CH2:23][N:22]1[CH2:24][C:25]([F:28])([F:26])[F:27]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11733311methyl (R)-8-[3-(2-pyridylamino)-1-propyloxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

Product 1

HCID 11762165[3-Oxo-8-[3-(pyridin-2-ylamino)-propoxy]-2-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-acetic acidYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (25 mg, 0.6 mmole) was added to a solution of methyl (R)-8-[3-(2-pyridylamino)-1-propyloxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.25 g, 0.54 mmole) in THF (5 mL) and H2O (2 mL) at RT. After 18 hr, the reaction was concentrated to dryness and the residue was dissolved in H2O (4 mL). The solution was carefully brought to pH≈4 with 3.0 N HCl. The precipitate was collected and dried in high vacuum at 40-45° C. to afford the title compound (0.15 g, 62%) as an off-white solid: MS (ES) m/e 452.1 (M+H)+. Anal. Calcd for C22H24F3N3O4. 0.5 H2O: C, 57.38; H, 5.47; N, 9.12. Found: C, 57.72; H, 5.24; N, 8.92.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. dissolutionthe residue was dissolved in H2O (4 mL)
  3. customThe precipitate was collected
  4. customdried in high vacuum at 40-45° C.

Sources & evidence

ORD record
ord-4e14d296d10f46378ab2a92afff96b43
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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