Sodium Hydroxide → HCID 19956086, compound

HRID 1779687Notes

Reaction equation

HRID 1779687 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]([CH2:15][N:16]3[CH2:21][CH2:20][C:19]([C:28]([O:30]CC)=[O:29])([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:18][CH2:17]3)[O:12][C:11]2=[O:33])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[OH-].[Na+]>CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]([CH2:15][N:16]3[CH2:21][CH2:20][C:19]([C:28]([OH:30])=[O:29])([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][CH2:17]3)[O:12][C:11]2=[O:33])=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9868876HCID 9868876, compound

Product 1

HCID 19956086HCID 19956086, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.8 g of 3-(4-amidinophenyl)-5-(4-ethoxycarbonyl-4-ethoxycarbonylmethylpiperidinomethyl)-oxazolidin-2-one [obtainable accord to Ex. 9] are suspended in 60 ml of methanol, treated with 10 ml of 2N of NaOH solution and stirred at room temperature for 4 hours. After removal of the solvent, the residue is taken up in water, the pH is adjusted to 3 by addition of dilute HCl and the reaction mixture is filtered through an ion exchanger. After extraction with ethyl acetate the filtrate is dried over MgSO4. After removal of the solvent and subsequent freeze-drying, 3-(4-amidinophenyl)-5-(4-carboxy-4-carboxymethylpiperidinomethyl)oxazolidin-2-one is obtained.

Workup

  1. customAfter removal of the solvent
  2. additionthe pH is adjusted to 3 by addition of dilute HCl
  3. filtrationthe reaction mixture is filtered through an ion exchanger
  4. extractionAfter extraction with ethyl acetate the filtrate
  5. dry with materialis dried over MgSO4
  6. customAfter removal of the solvent and subsequent freeze-drying

Sources & evidence

ORD record
ord-36a43e455ec24791ad30d7d810a046e4
Source dataset
uspto-grants-1997_05
Patent number
US05627197

Reaction notes

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