Acetic Acid → Ethyl 3-(2-fluoro-4-{[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

HRID 508068Notes

Reaction equation

HRID 508068 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:21]([F:32])[CH:20]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:32][C:21]1[CH:20]=[C:19]([NH:18][CH2:15][C:11]2[CH:10]=[C:9]([C:5]3[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]=3[CH3:17])[CH:14]=[CH:13][CH:12]=2)[CH:24]=[CH:23][C:22]=1[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehydeHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoate

Product 1

HCID 23157575Ethyl 3-(2-fluoro-4-{[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoateYield 66%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (1.05 g, 4.64 mmol), ethyl 3-(4-amino-2-fluorophenyl)propanoate. (1.00 g, 4.73 mol), acetic acid (0.80 mL, 14 mmol) and 1,2-dichloroethane (20 mL) was stirred at room temperature for 2 hr, and sodium triacetoxyborohydride (3.00 g, 14.2 mmol) was added. The mixture was stirred overnight at room temperature and concentrated. Ethyl acetate was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The mixture was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give the title compound (1.29 g, yield 66%) as a yellow oil.

Workup

  1. concentrationconcentrated
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe mixture was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7176939976d4442a9a98cb1fd9e451a4
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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