Hydrochloric Acid → HCID 22063479, compound

HRID 12114Notes

Reaction equation

HRID 12114 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:42])[CH2:21][NH:22][C:23]([CH3:41])([CH3:40])[CH2:24][C:25]2[CH:39]=[CH:38][C:28]([O:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:27][CH:26]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:42])[CH2:21][NH:22][C:23]([CH3:40])([CH3:41])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:38][CH:39]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22063472HCID 22063472, compound

Product 1

HCID 22063479HCID 22063479, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.00 g (1.73 mmol) of ethyl 4-(4-{2-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo [1,4]oxazin-8-yl)-2-hydroxyethylamino]-2-methylpropyl}phenoxy)butyrate in 25 mL methanol is combined with 2.5 mL of 1 N sodium hydroxide solution, refluxed for 30 minutes, and then neutralized with 1 N hydrochloric acid. The solution is evaporated down and the residual oil is dissolved by heating in 5 mL of n-butanol. After the addition of a crystallization aid, a solid is precipitated out which is suction filtered and washed with acetone and diethyl ether. Yield: 0.75 g (79%); melting point: 216° C.-218° C.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe solution is evaporated down
  3. dissolutionthe residual oil is dissolved
  4. temperatureby heating in 5 mL of n-butanol
  5. additionAfter the addition of a crystallization aid
  6. customa solid is precipitated out which
  7. filtrationfiltered
  8. washwashed with acetone and diethyl ether

Sources & evidence

ORD record
ord-db2eb28b40bd4d06ac41f90d4b5af7df
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

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