Acetic Acid → Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate

HRID 508085Notes

Reaction equation

HRID 508085 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=2)=[C:9]([CH3:23])[C:8]=1[CH3:24])[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]([F:39])[CH:27]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:24])=[C:9]([CH3:23])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]([F:39])[CH:27]=3)[CH:16]=2)=[C:11]([CH3:14])[C:12]=1[CH3:13])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoateHCID 231575154'-(2-Ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-carbaldehyde

Product 1

HCID 23157425Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoateYield 84%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4′-(2-ethoxyethoxy)-2′,3′,5′,6′-tetramethylbiphenyl-3-carbaldehyde (0.300 g, 0.99 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.194 g, 0.99 mmol) in 1,2-dichloroethane (7.0 mL) was added acetic acid (0.158 mL, 2.76 mmol), and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.585 g, 2.76 mmol) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.400 g, yield 84%) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred for 3 hr
  2. washwashed with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-6bc5ed880ce0488aa198be60e8e4e489
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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