Tetrahydrofuran → HCID 18518357, compound

HRID 1369247Notes

Reaction equation

HRID 1369247 reaction equation
[N:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([O:25]CC)=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1.O.[OH-].[Li+].C1COCC1>O>[N:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([OH:25])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54532291HCID 54532291, compound

Product 1

HCID 18518357HCID 18518357, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl (±)-10,11-dihydro-3-[3-(3,4,5,6-tetrahydropyrimid-2-ylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (0.17 g, 0.36 mmol), lithium hydroxide monohydrate (0.042 g, 1 mmol), THF (3 mL), and water (10 mL) was stirred at room temperature for 20 hr, then was concentrated. The residue was dissolved in water, and the solution was brought to pH 4 with 3 N HCl. The resulting solution was kept in the refrigerator overnight, then the supernatant was decanted away from the solid. The solid was dried in vacuum to give the title compound (0.145 g, 91%) as a tan solid: MS (ES) 408.3 (M+H)+. Anal. Calcd for C24H29N3O3.1.3 HCl: C, 63.37; H,6.71; N, 9.23. Found: C, 63.67; H, 6.84; N, 9.46.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in water
  3. customwas kept in the refrigerator overnight
  4. customthe supernatant was decanted away from the solid
  5. customThe solid was dried in vacuum

Sources & evidence

ORD record
ord-abaef289569f4099affd518118d574b0
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

Loading…