3-(4-Hydroxyphenyl)propionic acid → HCID 69058599, compound

HRID 1866158Notes

Reaction equation

HRID 1866158 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.Cl.[NH2:14][CH2:15][C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[OH:17].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:24][C:20]1[CH:19]=[C:18]([C@@H:16]([OH:17])[CH2:15][NH:14][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:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 56846012(R)-2-Amino-1-(3-chlorophenyl) ethanol hydrochloride

Product 1

HCID 69058599HCID 69058599, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(4-hydroxyphenyl)propanoic acid (15.0 g), (1R)-2-amino-1-(3-chlorophenyl)ethanol hydrochloride (18.8 g), and 1-hydroxybenzotriazole (14.6 g) in N,N-dimethylformamide (100 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26.0 g), and the mixture was stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed successively with sodium bicarbonate solution and brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-3-(4-hydroxyphenyl)propanamide (11.61 g) as a white amorphous powder.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed successively with sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-764e143817924306a609096fd83b1ba5
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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