Hydroxyamine hydrochloride → E-3-[3'-(1-adamantyl)-4'-hydroxy-biphenyl-4-yl]-N-hydroxy-acrylamide

HRID 12988Notes

Reaction equation

HRID 12988 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:18]4[CH:28]=[CH:27][C:21](/[CH:22]=[CH:23]/[C:24](O)=[O:25])=[CH:20][CH:19]=4)[CH:14]=[CH:15][C:16]=3[OH:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH2:29].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.Cl.[NH2:53]O>CN(C=O)C>[C:1]12([C:11]3[CH:12]=[C:13]([C:18]4[CH:28]=[CH:27][C:21](/[CH:22]=[CH:23]/[C:24]([NH:53][OH:29])=[O:25])=[CH:20][CH:19]=4)[CH:14]=[CH:15][C:16]=3[OH:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9864378AdaroteneHCID 178526939HCID 178526939, compound

Product 1

HCID 15986417E-3-[3'-(1-adamantyl)-4'-hydroxy-biphenyl-4-yl]-N-hydroxy-acrylamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of E-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid (2 g, 5.34 mmol) in 80 ml of DMF were added hydroxybenzotriazole hydrate (866 mg, 5.34 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1130 mg, 6.94 mmol). The mixture was stirred at room temperature for 4 h. After addition of hydroxylamine hydrochloride (1856 mg, 26.7 mmol), followed by 3.7 ml (26.7 mmol) of TEA, the mixture was stirred at room temperature overnight. DMF was removed under reduced pressure and the residue was washed with water to obtain 5 g of a crude product. Purification by flash chromatography on silica gel (phosphate buffered) using as eluent dichloromethane/methanol 95:5 afforded 950 mg of the title compound as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customDMF was removed under reduced pressure
  3. washthe residue was washed with water
  4. customto obtain 5 g of a crude product
  5. customPurification by flash chromatography on silica gel (phosphate buffered)

Sources & evidence

ORD record
ord-f163181057ab418cbb790b50f176beec
Source dataset
uspto-grants-2010_06
Patent number
US07728039B2

Reaction notes

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