Dicyclohexylcarbodiimide → HCID 73212385, compound

HRID 1773073Notes

Reaction equation

HRID 1773073 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[OH:20])[C:14](O)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O[N:22]1[C:26](=O)[CH2:25][CH2:24][C:23]1=[O:28].[CH:29]1(N=C=NC2CCCCC2)[CH2:34]CCC[CH2:30]1.[O:44]1CCOCC1>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[OH:20])[C:14]([NH:22][CH2:26][C:25]3[CH:34]=[CH:29][C:30]([OH:44])=[C:23]([OH:28])[CH:24]=3)=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 312751,4-DioxaneHCID 80170N-HydroxysuccinimideHCID 16784433HCID 16784433, compound

Product 1

HCID 73212385HCID 73212385, compound

Procedure

3-Adamantan-1-yl-4-hydroxybenzoic acid (0.286 g), N-hydroxysuccinimide (0.12 g) and N,N′-dicyclohexylcarbodiimide (0.22 g) are dissolved in dioxane (5 mL) and stirred for 12 hours. The produced solid is filtered and the filtrate is added dropwise to a mixture solution of 3,4-dihydroxybenzylamine bromate (0.25 g), sodium bicarbonate (0.09 g) and water (1 mL). After stirring at 50° C. for 2 hours, the solution is cooled to room temperature, neutralized with 10% HCl solution and washed with ethyl acetate (30 mL). The organic layer is dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and separated by column chromatography to obtain 0.03 g of the target compound as white solid.

Workup

  1. filtrationThe produced solid is filtered
  2. additionthe filtrate is added dropwise to a mixture solution of 3,4-dihydroxybenzylamine bromate (0.25 g), sodium bicarbonate (0.09 g) and water (1 mL)
  3. stirringAfter stirring at 50° C. for 2 hours
  4. washwashed with ethyl acetate (30 mL)
  5. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customseparated by column chromatography

Sources & evidence

ORD record
ord-3bbb8b319e424e5ea73daea4df9068d3
Source dataset
uspto-grants-2016_02
Patent number
US09254251B2

Reaction notes

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