Sodium Hydroxide → Ethanol ammonium hydroxide water

HRID 618145Notes

Reaction equation

HRID 618145 reaction equation
[C:1]([C:8]1[C:13](N)=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH3:21])=[O:19])[CH:11]=[CH:10][N:9]=1)(OC(C)(C)C)=[O:2].C([O:28][C:29](=[O:44])[CH2:30][C@@H:31]([CH2:33][CH2:34][C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:37][CH:36]=1)[NH2:32])C.[OH-:45].[Na+]>CCO.CCOC(C)=O>[CH3:8][CH2:1][OH:2].[OH2:28].[NH4+:9].[OH-:45].[NH2:32][C:8]1[CH:13]=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH3:21])=[O:19])[CH:11]=[CH:10][N:9]=1.[NH:37]1[C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:35]([CH2:34][CH2:33][C@H:31]([CH2:30][C:29]([OH:44])=[O:28])[NH2:32])=[CH:36]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67601154HCID 67601154, compound

Product 2

HCID 86596525Ethanol ammonium hydroxide waterHCID 86754473HCID 86754473, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ester 4-5 (20 mg, 34 μmol) was dissolved in 350 μL EtOH, then 1 N NaOH (85 μL, 85 μmol) was added. After 2 h the reaction was diluted with EtOAc, washed with 10% KHSO4 and brine, dried (MgSO4), filtered and concentrated. The residue was dissolved in 1 mL CH2Cl2, treated with 1 mL TFA for 1 h, then concentrated and azeotroped with toluene. Flash chromatography (silica, 50:1:1, EtOH/H2O/NH4OH) provided 4-6 as an off-white solid.

Workup

  1. washwashed with 10% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 1 mL CH2Cl2
  6. additiontreated with 1 mL TFA for 1 h
  7. concentrationconcentrated
  8. customazeotroped with toluene

Sources & evidence

ORD record
ord-15151bcfb982467eb47379859d4c787b
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

Loading…