3-(4-Hydroxyphenyl)propionic acid → HCID 9824710, compound

HRID 1292371Notes

Reaction equation

HRID 1292371 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.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([C:45]2[NH:46][C:47]3[C:52]([C:53]=2[CH2:54][CH2:55][NH2:56])=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:40]=[CH:41][C:42]=1[O:43][CH3:44]>>[CH3:35][O:36][C:37]1[CH:38]=[C:39]([C:45]2[NH:46][C:47]3[C:52]([C:53]=2[CH2:54][CH2:55][NH:56][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:51][CH:50]=[CH:49][CH:48]=3)[CH:40]=[CH:41][C:42]=1[O:43][CH3:44]

Participants

5

Reactant 4

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 368016595426-76-9

Product 1

HCID 9824710HCID 9824710, compoundYield 106.1%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-(4-hydroxyphenyl)propionic acid (80 mg in 4 mL N,N-dimethylformamide) was added 1-hydroxybenzotriazole (78 mg) and the mixture cooled to 0° C. After 10 minutes, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (130 mg) was added. The mixture was warmed to room temperature and 2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]ethylamine (272 mg) was added. After 17 hours the reaction was quenched by the addition of water and extracted with ethyl acetate. The organic portion was washed with water, 0.5M sodium bisulfate and brine, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol, 95:5) gave the title compound (227 mg). m/e=444 (M)

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. customAfter 17 hours the reaction was quenched by the addition of water
  3. extractionextracted with ethyl acetate
  4. washThe organic portion was washed with water, 0.5M sodium bisulfate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-5f8dd1af42414588b5802032d16401f7
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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