Sodium Hydroxide → 5-Benzylsulfonylamino-1-methoxymethyl-3-uracilylacetic acid

HRID 849296Notes

Reaction equation

HRID 849296 reaction equation
[CH2:1]([S:8]([NH:11][C:12]1[C:13](=[O:28])[N:14]([CH2:22][C:23]([O:25]CC)=[O:24])[C:15](=[O:21])[N:16]([CH2:18][O:19][CH3:20])[CH:17]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[CH2:1]([S:8]([NH:11][C:12]1[C:13](=[O:28])[N:14]([CH2:22][C:23]([OH:25])=[O:24])[C:15](=[O:21])[N:16]([CH2:18][O:19][CH3:20])[CH:17]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22943410Ethyl 5-benzylsulfonylamino-1-methoxymethyl-3-uracilylacetate

Product 1

HCID 229433865-Benzylsulfonylamino-1-methoxymethyl-3-uracilylacetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a cooled (0° C.) suspension of the compound of Example 43 (10.0 g, 24 mmole) in methanol (50 mL) is added 1.0N NaOH (49 mL) over a period of 10 minutes. After the addition is complete, the solution is allowed to warm to room temperature over a period of 1.5 hours. The solvent is reduced under vacuum, residue diluted with water, and washed with ethyl acetate twice. The aqueous layer is acidified with 2.0N HCl to pH 1, extracted with ethyl acetate three times. The combined organic extracts are washed with water, then brine (twice). The solvent is removed to give the title compound.

Workup

  1. temperatureTo a cooled
  2. additionAfter the addition
  3. washwashed with ethyl acetate twice
  4. extractionextracted with ethyl acetate three times
  5. washThe combined organic extracts are washed with water
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-1b7f83d16fdb4ffc8e52082b5ad0cc21
Source dataset
uspto-grants-2000_01
Patent number
US06011158

Reaction notes

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