Potassium Hydroxide → HCID 15282610, compound

HRID 1186015Notes

Reaction equation

HRID 1186015 reaction equation
[CH2:1]([C:8]1([C:23]([O:25]CC)=[O:24])[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([C:8]1([C:23]([OH:25])=[O:24])[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 71250030HCID 71250030, compound

Product 1

HCID 15282610HCID 15282610, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of compound 2 (8.0 g, 21.79 mmol) in CH3OH (20 mL) was added 2N aqueous KOH (20 mL) and heated up to 100° C. and stirred for 16 h. The volatiles were evaporated under reduced pressure. The residue obtained was diluted with ice cold water (50 mL) and washed with ether (50 mL). The aqueous layer was acidified to pH˜2 using HCl solution and extracted with EtOAc (2×100 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford compound 3 (6 g, 81%) as an off white solid.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customThe residue obtained
  3. washwashed with ether (50 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e678790f1b443d090d4611cee4de4e1
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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