Sodium Hydroxide → HCID 22116154, compound

HRID 1276378Notes

Reaction equation

HRID 1276378 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:27][CH2:28][CH2:29][O:30][CH3:31])[C:23]([O:25]C)=[O:24])=[CH:17][CH:16]=1)[CH3:11].[OH-].[Na+]>CO.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:27][CH2:28][CH2:29][O:30][CH3:31])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=1)[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22116160HCID 22116160, compound

Product 1

HCID 22116154HCID 22116154, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(2-methoxyethoxy)propanoate (1.08 g, Int. Patent Appl., Publication No. WO 9401420) and sodium hydroxide (253 mg) in methanol:water (1:1, 10 mL) was heated under reflux for 2 hours. After evaporation of the resultant mixture in vacuo, the residue was diluted with water, acidified to pH 5 with 2M hydrochloric acid and then extracted with ethyl acetate. Washing of the ethyl acetate extracts with water and drying (MgSO4) and evaporation gave the title compound as an oil which crystallised on trituration with diethyl ether/hexane. [Found C, 63.8; H, 6.5; N, 7.0%; M+ 414.1791. C22H26N2O6 requires C, 63.8; H, 6.3; N, 6.8%; M+ 414.1791]; δH (CDCl3) 2.91 (1H,dd), 3.15 (1H,dd), 3.34 (3H,s), 3.38 (3H,s), 3.41-3.69 (4H,m), 3.93 (2H,t), 4.05 (1H,dd), 4.21 (2H,t), 6.80 (2H,d) and 6.83-7.38 (6H m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of the resultant mixture in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washWashing of the ethyl acetate
  7. customdrying
  8. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-21289868dec248b49c4d697b8c763e79
Source dataset
uspto-grants-2000_12
Patent number
US06166049

Reaction notes

Loading…