Water → HCID 10806562, compound

HRID 1586227Notes

Reaction equation

HRID 1586227 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH2:10][C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[O:25]([NH2:27])[CH3:26].O>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH2:10][C:11]([NH:27][O:25][CH3:26])=[O:12])=[CH:17][CH:18]=1)#[N:23]

Participants

6

Reactant 3

HCID 962WaterHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10709631HCID 10709631, compound

Product 1

HCID 10806562HCID 10806562, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Part A. A solution of 3-(3-cyanophenyl)-5-(4-cyanophenyl)pentanoic acid (0.15 gm, 0.49 mmol), methoxylamine hydrochloride (0.041 gm, 0.54 mmol), 1-(3-dimethylaminopropyl)-3-ethhylcarbodiimide hydrochloride (0.14 gm, 0.73 mmol) and 4-dimethylaminopyridine (0.15 gm, 1.22 mmol) in 5 mLs DMF under a nitrogen atmosphere was stirred for 18 hrs. The reaction solution was poured into water and extracted with ethyl acetate. The combined organic layer was washed with 1 N HCl (2×), water, brine, dried over magnesium sulfate and concentrated to give the crude product as a colorless viscous oil. The product was purified by flash chromatography on silica gel (50 mLs) eluting methylene chloride:ethyl acetate (v:v, 60:40) to give 4-(cyano)-beta-(3-cyanophenyl)-N-methoxybenzene pentanamide as a colorless vicous oil 0.15 gm (91%) 1H NMR (CDCl3): 8.03(bs, 1H), 7.56-7.42(m, 6H), 7.15(d, 2H), 3.58(s, 3H), 3.28(m, 1H), 2.8-1.85(m, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with 1 N HCl (2×), water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude product as a colorless viscous oil
  6. customThe product was purified by flash chromatography on silica gel (50 mLs)
  7. washeluting methylene chloride

Sources & evidence

ORD record
ord-edc67f5966aa4c6887492f122f5ccf11
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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