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

HRID 397011Notes

Reaction equation

HRID 397011 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-f05dd0b8cd024ebe844b2c779d52509f
Source dataset
uspto-grants-2003_08
Patent number
US06608204B1

Reaction notes

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