Water → HCID 10155946, compound

HRID 2416711Notes

Reaction equation

HRID 2416711 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:29]=[CH:28][C:15]2[CH2:16][CH:17]([CH2:22][C:23]([O:25]CC)=[O:24])[C:18](=[O:21])[NH:19][CH2:20][C:14]=2[CH:13]=1.O.[OH-].[Li+].C1COCC1.O>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:29]=[CH:28][C:15]2[CH2:16][CH:17]([CH2:22][C:23]([OH:25])=[O:24])[C:18](=[O:21])[NH:19][CH2:20][C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54434818HCID 54434818, compound

Product 1

HCID 10155946HCID 10155946, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl (±)-8-[3-(2-pyridylamino)-1-propyloxy]-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.7 g, 2 mmol), lithium hydroxide monohydrate (0.12 g, 3 mmol), 5 mL THF (5 mL), H2O (5 mL), and MeOH (2 mL) was stirred at room temperature for 18 hr, then was then concentrated. The residue was partitioned between ethyl acetate and water, and the layers were separated. The aqueous phase was cautiously brought to pH 4 with 3 N HCl and allowed to stand. The resulting crystals were collected by filtration and dried to give the title compound (0.4 g, 65%) as a tan solid: MS m/e 370.4 (M+H)+. Anal. Calcd for C20H23N3O4.0.25 H2O: C, 64.25; H, 6.34; N, 11.24. Found: C, 64.02; H, 6.37; N, 11.20.

Workup

  1. concentrationwas then concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-52c3b727619e4202a48f31eb720185ca
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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