3-(4-Hydroxyphenyl)propionic acid → HCID 69120490, compound

HRID 899876Notes

Reaction equation

HRID 899876 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.[F:13][C:14]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:15]=1[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].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>[F:13][C:14]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:15]=1[CH2:16][N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 60663854N-(2,4-difluorobenzyl)-N-heptylamine

Product 1

HCID 69120490HCID 69120490, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Hydroxyphenyl)propionic acid (108 mg, 0.650 mmol) was dissolved in DMF. N-(2,4-difluorobenzyl)-N-heptylamine (164.7 mg, 0.682 mmol) was added. The mixture was cooled in an ice-bath. TBTU (219 mg, 0.682 mmol) was added and followed by DIPEA (0.238 ml, 1.365 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 with 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 223 mg desired product, yield 88%.

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 with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-0ebb6f182eb345b38dfe864bb0f1a213
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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