Hydrochloric Acid → 4-(4-Benzylamino-3-hydroxy-phenyl)-3-methyl-4-oxo-butyric acid

HRID 1619965Notes

Reaction equation

HRID 1619965 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[CH:16]([CH:18](C(O)=O)[C:19]([OH:21])=[O:20])[CH3:17])=[CH:11][C:10]=1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)COCCO.COC.C(OC(C)C)(C)C.Cl>O>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[CH:16]([CH3:17])[CH2:18][C:19]([OH:21])=[O:20])=[CH:11][C:10]=1[OH:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 212256572-(2-Hydroxyethoxy)ethanol;methoxymethaneHCID 674670302-[2-(4-Benzylamino-3-hydroxy-phenyl)-1-methyl-2-oxo-ethyl]-malonic acid

Product 1

HCID 674661774-(4-Benzylamino-3-hydroxy-phenyl)-3-methyl-4-oxo-butyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

78.9 g (220.8 mmol) 2-[2-(4-benzylamino-3-hydroxy-phenyl)-1-methyl-2-oxo-ethyl]-malonic acid are combined with 200 ml diethyleneglycol-dimethylether and stirred for 3 h at 140° C. The mixture is combined with water and diisopropylether, then it is adjusted with 6N hydrochloric acid to pH=2 and extracted with DCM. The org. phase is separated off and dried on magnesium sulphate, then the solv. is eliminated by rotary evaporation i.V., the residue is stirred with diisopropylether and filtered off.

Workup

  1. extractionextracted with DCM
  2. customphase is separated off
  3. customdried on magnesium sulphate
  4. stirring, the residue is stirred with diisopropylether
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-c9736f84cf7f46008f3683e08e20853f
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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