(4-Nitrophenyl)acetic acid → HCID 19873419, compound

HRID 466358Notes

Reaction equation

HRID 466358 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:15].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11](=[O:13])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:15]

Participants

7

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 480381-Heptanamine, N-ethyl-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 19873419HCID 19873419, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-nitrophenylacetic acid (7.14 g, 0.0394 mol), ethylheptylamine (5.64 g, 0.0394 mol) and 1-hydroxybenzotriazole (6.0 g, 0.044 mol) in 35 ml of dimethylformamide (DMF), under nitrogen, is cooled in an ice bath. The mixture is then treated with the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (7.68 g, 0.04 mol) in portions over 15 min. The mixture is stirred in the cold for 1 hr and at room temperature overnight. The mixture is diluted with 400 ml of ethyl acetate and washed twice with saturated NaHCO3. (Each wash is back extracted with ethyl acetate.) The pooled organic extract is washed sequentially with water (50 ml), 1N KHSO4 solution (3×50 ml), water (50 ml) and finally brine (50 ml). It is dried (Na2SO4) and concentrated in vacuo to yield the title compound. This residue is treated with Et2O-pentane, a solid filtered off and the filtrate concentrated in vacuo. The residue is chromatographed over 1400 ml of silica gel with 25% EtOAc-SSB with 42 ml fractions being collected. Fractions at approximately 70-104 yield the title compound as an oil.

Workup

  1. temperatureunder nitrogen, is cooled in an ice bath
  2. customat room temperature
  3. customovernight
  4. washwashed twice with saturated NaHCO3
  5. extraction(Each wash is back extracted with ethyl acetate
  6. extraction) The pooled organic extract
  7. washis washed sequentially with water (50 ml), 1N KHSO4 solution (3×50 ml), water (50 ml) and finally brine (50 ml)
  8. dry with materialIt is dried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63e7a3dde80a49309817c4c7e08388b1
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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