Sodium Hydroxide → HCID 57987478, compound

HRID 1869770Notes

Reaction equation

HRID 1869770 reaction equation
C[CH:2]([C@@H:6]1[CH2:11][CH2:10][N:9]([C@@H:12]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]=[CH2:26])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C@H:8]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH2:7]1)[C:3]([O-:5])=[O:4].[OH-].[Na+]>CO>[CH2:24]([C:21]1[CH:22]=[CH:23][C:18]([C@H:12]([N:9]2[CH2:10][CH2:11][C@@H:6]([CH2:2][C:3]([OH:5])=[O:4])[CH2:7][C@H:8]2[C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:19][CH:20]=1)[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86618004HCID 86618004, compound

Product 1

HCID 57987478HCID 57987478, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The ester from Step 1 (100 mg) was dissolved in methanol (1 mL) and sodium hydroxide (0.3 mL, 4N) was added. The mixture was heated at 60° C. overnight, cooled, evaporated and the residue dispersed between CH2Cl2 and HCl (0.1N). The organic extract was separated and washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using 10-95% ethyl acetate in iso-hexane as eluant.

Workup

  1. temperaturecooled
  2. customevaporated
  3. additionthe residue dispersed between CH2Cl2 and HCl (0.1N)
  4. extractionThe organic extract
  5. customwas separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified on silica using 10-95% ethyl acetate in iso-hexane as eluant

Sources & evidence

ORD record
ord-8f4c313ea9ac4b20984a2b86ed53a9d0
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

Loading…