Potassium Hydroxide → HCID 22252085, compound

HRID 2243616Notes

Reaction equation

HRID 2243616 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-08dfb07b35da426d8401644fd4143d0d
Source dataset
uspto-grants-2010_03
Patent number
US07674773B2

Reaction notes

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