Citric Acid → HCID 69235620, compound

HRID 394556Notes

Reaction equation

HRID 394556 reaction equation
C[O:2][C:3](=O)[CH2:4][C@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Li+].C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:20][C:17]([O:16][C:14](=[O:15])[NH:13][C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:4][CH2:3][OH:2])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 4148881Lithium borohydride2×HCID 10447103Methyl (βR)-β-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoate

Product 1

HCID 69235620HCID 69235620, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (R)-β-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzenebutanoic acid methyl ester (1.5 g, 5.1 mmol, J. Med. Chem. 1985, 28, 434) in THF (10 mL), was added lithium borohydride (218 mg, 10 mmol), followed by ethanol (10 mL), dropwise. After stirring at rt for 18 hours, an additional lithium borohydride (218 mg 10 mmol) was added and stirring continued for 6 hours. The reaction mixture was ice cooled and adjusted to pH 4 by the addition of a 10% citric acid solution. Organic solvents were removed and the resulting cloudy aqueous solution was extracted with dichloromethane. The extracts were combined, dried (MgSO4) and concentrated in vacuo to afford a clear colorless oil residue which was purified by flash chromatography on silica gel eluting with 30% ethyl acetate in hexanes to yield (1.2 g, 89%) of the title compound as a clear colorless oil. MS; (M+H)+=266

Workup

  1. stirringstirring
  2. waitcontinued for 6 hours
  3. temperaturecooled
  4. customOrganic solvents were removed
  5. extractionthe resulting cloudy aqueous solution was extracted with dichloromethane
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a clear colorless oil residue which
  9. customwas purified by flash chromatography on silica gel eluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8f6100843be8492c9361c8bd8ca5e12c
Source dataset
uspto-grants-2003_08
Patent number
US06602883B1

Reaction notes

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