Sodium Hydroxide → HCID 54161735, compound

HRID 266393Notes

Reaction equation

HRID 266393 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]CC)=[O:24])=[CH:18][CH:17]=2)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@@H:12]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=2)=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54294382HCID 54294382, compound

Product 1

HCID 54161735HCID 54161735, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-(4-bromobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-3-phenylpropanamide (17.0 g) was dissolved in methanol (200 ml) and cooled to 0° C. After 2N NaOH (46.8 ml) was added, the whole was stirred at room temperature overnight under argon. The reaction mixture was concentrated under reduced pressure to remove methanol. The concentrate was poured to 6N HCl while cooling with ice. The precipitated crystal was filtered and recrystallized from acetonitrile to obtain (S)-2-(4-bromobenzenesulfonylamino)-N-(4-(carboxymethyl)phenyl)-3-phenylpropanamide (1.10 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove methanol
  3. additionThe concentrate was poured to 6N HCl
  4. temperaturewhile cooling with ice
  5. filtrationThe precipitated crystal was filtered
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-d84c221a501d43ea9f9cad51d527d415
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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