Sodium Hydroxide → HCID 53721136, compound

HRID 1491810Notes

Reaction equation

HRID 1491810 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH:4]([C:18]([O:20]CC)=[O:19])[CH2:3]1.[OH-].[Na+]>C(O)C>[CH3:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH:4]([C:18]([OH:20])=[O:19])[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86748298HCID 86748298, compound

Product 1

HCID 53721136HCID 53721136, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8.95 g (29.3 mmol) of Part (3) compound in 90 mL of absolute ethanol cooled in an ambient water bath was added 90 mL of 1N aq NaOH solution. The reaction mixture was stirred for 16 h then concentrated in vacuo to ~1/2 volume to remove ethanol. The residue was partitioned between 100 mL of 1M aq HCl solution and 100 mL of ether. The aqueous layer was separated and extracted with two-50 mL portions of ether. The ether extracts were combined, dried (magnesium sulfate) and concentrated in vacuo to afford 8.15 g (29.4 mmol, 100%) of title compound as a colorless oil.

Workup

  1. concentrationthen concentrated in vacuo to ~1/2 volume
  2. customto remove ethanol
  3. customThe residue was partitioned between 100 mL of 1M aq HCl solution and 100 mL of ether
  4. customThe aqueous layer was separated
  5. extractionextracted with two-50 mL portions of ether
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b6ead60be02495fa169e5bd7f9f3f2f
Source dataset
uspto-grants-1994_12
Patent number
US05371091

Reaction notes

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