Sodium Hydroxide → HCID 19032831, compound

HRID 266321Notes

Reaction equation

HRID 266321 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:35])[CH:17]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:11][CH:10]=1)=[O:7])C>C(O)C>[C:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:35])[CH:17]([NH:24][S:25]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:11][CH:10]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19032758HCID 19032758, compound

Product 1

HCID 19032831HCID 19032831, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2N NaOH (1.085 ml) was added to a solution of (RS)-N-(4-(ethoxycarbonylmethyl)phenyl)-2-(4-fluorobenzenesulfonyl-amino)-3-(1H-imidazol-1-yl)propanamide (103 mg) in ethanol (5 ml) and the whole was stirred for 5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, washed with ethyl acetate 3 times, neutralized by 2N HCl (1.085 ml), and then extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution and dried over Na2SO4. The solvent was evaporated under reduced pressure to obtain (RS)-N-(4-(carboxymethyl)phenyl)-2-(4-fluorobenzenesulfonylamino)-3-(1H-imidazol-1-yl)propanamide (34.3 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl acetate 3 times
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with a saturated saline solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e42978f761146ac8ac96d4e910e1574
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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