Potassium Hydroxide → HCID 22252085, compound

HRID 1725291Notes

Reaction equation

HRID 1725291 reaction equation
[CH2:1]([N:8]([CH2:17][CH:18]([OH:27])[CH:19]([OH:26])[CH:20]([OH:25])[CH:21]([OH:24])[CH2:22][OH:23])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[CH2:1]([N:8]([CH2:17][CH:18]([OH:27])[CH:19]([OH:26])[CH:20]([OH:25])[CH:21]([OH:24])[CH2:22][OH:23])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22252065HCID 22252065, compound

Product 1

HCID 22252085HCID 22252085, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, 0.46 g of methyl 5-[benzyl-(2,3,4,5,6-pentahydroxyhexyl)amino]pentanoate is dissolved in a mixture of 5 ml of ethanol and 5 ml of water, 0.4 g of potassium hydroxide is added and the mixture is stirred at 80° C. for 2 h. The cooled reaction mixture is then concentrated under reduced pressure and the residue is taken up in water, neutralized with hydrochloric acid and again concentrated. The crude product is suspended in ethanol, the suspension is filtered and the filtrate is concentrated under reduced pressure. This gives 5-[benzyl-(2,3,4,5,6-pentahydroxyhexyl)amino]pentanoic acid of molecular weight 371.43 (C18H29NO7); MS (ESI): 372.2 (M+H+).

Workup

  1. additionis added
  2. customThe cooled reaction mixture
  3. concentrationis then concentrated under reduced pressure
  4. concentrationagain concentrated
  5. filtrationthe suspension is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4a85ace13763413ba731119f17e80772
Source dataset
uspto-grants-2009_02
Patent number
US07488829B2

Reaction notes

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