Sodium Hydroxide → HCID 68489568, compound

HRID 1822477Notes

Reaction equation

HRID 1822477 reaction equation
C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:14](=[O:24])[N:13]1[CH:9]([CH2:10][CH:11]([O:25][C:26]3[C:35]4[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=4)[N:29]=[C:28]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:27]=3)[CH2:12]1)[C:8](=[O:44])[NH:7]2)=[O:5])C.[OH-].[Na+]>CO>[CH3:37][O:36][C:32]1[CH:31]=[C:30]2[C:35]([C:26]([O:25][CH:11]3[CH2:10][CH:9]4[N:13]([C:14](=[O:24])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:44])[CH2:23]5)[CH2:12]3)=[CH:27][C:28]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[N:29]2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68492858HCID 68492858, compound

Product 1

HCID 68489568HCID 68489568, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Compound 139 (55 mg, mol) was dissolved in 2 ml of methanol and mixed with 3 eq. of aqueous NaOH and heated for 2 h at 60° C. in a closed vial. The reaction mixture was then extracted into ethyl acetate. The water solution was collected and acidified with 1N HCl solution to pH 2. The resulting solution was concentrated by rotary evaporation, dissolved in methanol and purified by preparative HPLC (acetonitrile-water) to give 34 mg of the title product. Yield 65%. MS (M+H+) 571.

Workup

  1. extractionThe reaction mixture was then extracted into ethyl acetate
  2. customThe water solution was collected
  3. concentrationThe resulting solution was concentrated by rotary evaporation
  4. dissolutiondissolved in methanol
  5. custompurified by preparative HPLC (acetonitrile-water)

Sources & evidence

ORD record
ord-0e3cb9672eb04e57b123c69c01b8fa22
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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