Hydrochloric Acid → HCID 22618845, compound

HRID 617611Notes

Reaction equation

HRID 617611 reaction equation
[BH4-].[Li+].[CH2:3]([C:5]([NH:27][C:28](OC)=[O:29])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[C:6]([O:8]CC)=O)[CH3:4].Cl.C(OCC)(=O)C>O1CCCC1>[CH2:3]([C:5]1([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:18]=2)[CH2:6][O:8][C:28](=[O:29])[NH:27]1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 22618903HCID 22618903, compound

Product 1

HCID 22618845HCID 22618845, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (3.2 g) was added to a solution of ethyl 2-ethyl-2-methoxycarbonylamino-4-(4-benzyloxyphenyl)butanoate (29 g) in tetrahydrofuran (370 ml) and the mixture was refluxed under heating for 5 hours. 2 M Hydrochloric acid (40 ml) was added to the reaction mixture and the mixture was stirred for 2.5 hours. Ethyl acetate was added to the reaction mixture, the mixture was washed with water and a saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. Treatment of the residue with hexane and ethyl acetate gave the subject compound (11 g). Then, the mother liquid was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:2) to give the subject compound (11 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. washthe mixture was washed with water
  4. dry with materiala saturated brine and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-56cadaa5fda040cdad2f34714695c9d4
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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