Sodium Hydroxide → HCID 18626235, compound

HRID 1859756Notes

Reaction equation

HRID 1859756 reaction equation
[OH-:1].[Na+].C1(CO[C:11](=O)[CH2:12][C:13](=[O:32])[NH:14][C:15]2[CH:20]=[C:19]([C:21](=[O:29])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:16]=2[O:30][CH3:31])C=CC=CC=1>CO>[OH:1][CH:12]([C:11]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1)[C:13]([NH:14][C:15]1[CH:20]=[C:19]([CH:18]=[CH:17][C:16]=1[O:30][CH3:31])[C:21]([NH:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:29])=[O:32]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 54135704HCID 54135704, compound

Product 1

HCID 18626235HCID 18626235, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1N Sodium hydroxide (3 mL) was added to (2-methoxy-5-phenylcarbamoyl-phenylcarbamoyl)-acetic acid phenylmethyl ester from Example 252 (1.29 g, 3.1 mmol) in methanol (80 mL) and the reaction mixture boiled until most of the solvent was gone. Additional 1N sodium hydroxide (4 mL) and methanol (80 mL) were added and the mixture again concentrated to near dryness. Ethyl acetate (100 mL), water (100 mL), and 1N HCl (10 mL) were added, the layers separated, the organic layer washed with brine (50 μL), dried over magnesium sulfate, and concentrated to an oil. Trituration in hexanes/ethyl acetate (4:1) afforded the product (0.826 g); m.p. 173-175° C.

Workup

  1. concentrationthe mixture again concentrated
  2. additionEthyl acetate (100 mL), water (100 mL), and 1N HCl (10 mL) were added
  3. customthe layers separated
  4. washthe organic layer washed with brine (50 μL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-9af0f6e9a45041c5898431ffb2279962
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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