Hydrochloric Acid → HCID 22618862, compound

HRID 842289Notes

Reaction equation

HRID 842289 reaction equation
[BH4-].[Li+].[CH2:3]([C:5]([NH:30][C:31]([O:33][CH3:34])=[O:32])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:15][CH:14]=1)C(OCC)=O)[CH3:4].Cl.O>O1CCCC1>[CH2:3]([C:5]1([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:17][CH:18]=2)[CH2:34][O:33][C:31](=[O:32])[NH:30]1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 22618795HCID 22618795, compound

Product 1

HCID 22618862HCID 22618862, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (0.83 g) was added to a solution of ethyl 2-ethyl-2-methoxycarbonylamino-4-(4-(4-phenylbutyloxy)phenyl)butanoate (5.6 g) in tetrahydrofuran (130 ml) and the mixture was refluxed under heating for 4 hours and allowed to stand at room temperature overnight. 2M Hydrochloric acid (11 ml) and water (400 ml) were added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure. The residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1) to give the subject compound (3.0 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-004221eaee9945a8834d3e84f0fe6014
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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