Butyric Acid → Ethyl [4-({butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

HRID 1269618Notes

Reaction equation

HRID 1269618 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:33](O)(=[O:37])[CH2:34][CH2:35][CH3:36].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl>C(Cl)Cl>[C:33]([N:16]([CH2:15][C:13]1[CH:12]=[CH:11][C:3]([O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:2]([CH3:1])[CH:14]=1)[C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:27][CH:28]=2)[CH:20]=[CH:21][CH:22]=1)(=[O:37])[CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 5

HCID 264Butyric AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58622902Ethyl [2-methyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

Product 1

HCID 58622842Ethyl [4-({butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetateYield 48.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl [2-methyl-4-({[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)phenoxy]acetate (0.07 g, 0.16 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. under nitrogen was added butyric acid (0.016 mL, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (33 mg, 0.17 mmol) was then added in portions followed by triethylamine (0.022 mL, 0.16 mmol). After stirring for 15 mins at 0° C. the reaction was allowed to attain room temperature and stirred for 18 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and shaken with 1 M HCl (5 mL). The organic extract was separated by hydrophobic frit and the solvent removed in vacuo. Purification by Biotage™ chromatography (Silica, 12 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (40 mg).

Workup

  1. additionwas then added in portions
  2. customto attain room temperature
  3. stirringstirred for 18 h
  4. extractionThe organic extract
  5. customwas separated by hydrophobic frit
  6. customthe solvent removed in vacuo
  7. customPurification by Biotage™ chromatography (Silica, 12 g)
  8. washeluting 9:1 cyclohexane

Sources & evidence

ORD record
ord-078c54fe387e4bfbb78f8f0bf4e71f0b
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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