Acetic Acid → Ethyl 3-{4-[({4'-[2-(diethylamino)-2-oxoethoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoate

HRID 508051Notes

Reaction equation

HRID 508051 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=1.[CH2:16]([N:18]([CH2:39][CH3:40])[C:19](=[O:38])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=O)[CH:30]=2)=[C:24]([CH3:37])[CH:23]=1)[CH3:17].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCCl.O>[CH2:39]([N:18]([CH2:16][CH3:17])[C:19](=[O:38])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=3)[CH:30]=2)=[C:24]([CH3:37])[CH:23]=1)[CH3:40]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 311Citric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23157212N,N-diethyl-2-[(3'-formyl-2,6-dimethylbiphenyl-4-yl)oxy]acetamideHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoate

Product 1

HCID 23157525Ethyl 3-{4-[({4'-[2-(diethylamino)-2-oxoethoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoateYield 86%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.496 g, 2.35 mmol) and N,N-diethyl-2-[(3′-formyl-2,6-dimethylbiphenyl-4-yl)oxy]acetamide (0.725 g, 2.14 mmol) in 1,2-dichloroethane (10 mL) was added acetic acid (0.245 mL, 4.28 mmol), and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.907 q, 4.28 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 15 hr. Water and 10% aqueous citric acid solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-70% ethyl acetate/hexane) to give the title compound (0.978 g, yield 86%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (20%-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e1b593d2abeb422489429258cd9e8e26
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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