3-(4-Hydroxyphenyl)propionic acid → HCID 68871500, compound

HRID 2111977Notes

Reaction equation

HRID 2111977 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][NH:25][CH3:26])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][N:25]([CH3:26])[C:10](=[O:12])[CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

8

Reactant 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 77039N-MethylhomoveratrylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 68871500HCID 68871500, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Hydroxyphenyl)propionic acid (166.2 mg, 1 mmol) was dissolved in DMF (4 ml). 2-(3,4-Dimethoxyphenyl)-N-methylethylamine (211 mg, 1.05 mmol) was added. The mixture was cooled in an ice-bath. TBTU (337 mg, 1.05 mmol) was added, followed by DIPEA (0.37 ml, 2.1 mmol). The mixture was stirred overnight and the temperature was allowed up to room temperature. Ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.) were added and then the two phases were separated. The water phase was extracted with ethyl acetate. The organic phases were combined and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/15 ml) using DCM and then MeOH/DCM (1:99) as eluant gave 333 mg the desired product, yield 97%.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. customwas allowed up to room temperature
  3. customthe two phases were separated
  4. extractionThe water phase was extracted with ethyl acetate
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-47753e07327740eb95f69aaaaae731c9
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

Loading…