Hydrochloric Acid → 2-[2-(4-Benzylamino-3-hydroxy-phenyl)-1-methyl-2-oxo-ethyl]-malonic acid

HRID 1619964Notes

Reaction equation

HRID 1619964 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17](=[O:31])[CH:18]([CH:20]([C:26]([O:28]CC)=[O:27])[C:21]([O:23]CC)=[O:22])[CH3:19])=[CH:16][C:11]=2[O:10]C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[CH2:1]([NH:8][C:12]1[CH:13]=[CH:14][C:15]([C:17](=[O:31])[CH:18]([CH:20]([C:26]([OH:28])=[O:27])[C:21]([OH:23])=[O:22])[CH3:19])=[CH:16][C:11]=1[OH:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 67466180Diethyl 2-[2-(3-benzyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-1-methyl-2-oxo-ethyl]-malonate

Product 1

HCID 674670302-[2-(4-Benzylamino-3-hydroxy-phenyl)-1-methyl-2-oxo-ethyl]-malonic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g (11.4 mmol) diethyl 2-[2-(3-benzyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-1-methyl-2-oxo-ethyl]-malonate are combined with 50 ml of ethanol, then 28 ml 1N sodium hydroxide solution are added and the mixture is stirred overnight at RT. The next day another 28 ml of 1N sodium hydroxide solution are added and the mixture is refluxed for 6 h. After cooling to RT 50 ml 1N hydrochloric acid are added and the mixture is extracted with DCM. The phases are separated using a phase transfer cartridge. The filtrate is evaporated down i. V.

Workup

  1. temperaturethe mixture is refluxed for 6 h
  2. additionare added
  3. extractionthe mixture is extracted with DCM
  4. customThe phases are separated
  5. customThe filtrate is evaporated down i

Sources & evidence

ORD record
ord-2acfb75b7cfa407fa6d966a68c38ed75
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

Loading…