Sodium Hydroxide → HCID 131727857, compound

HRID 1994369Notes

Reaction equation

HRID 1994369 reaction equation
[CH:1]([S:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]([CH3:18])[C:15]([NH2:17])=[O:16])=[CH:10][CH:9]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[OH-].[Na+:20]>CO>[Na+:20].[CH:1]([S:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]([CH3:18])[C:15]([NH-:17])=[O:16])=[CH:10][CH:9]=1)(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59136415HCID 59136415, compound

Product 1

HCID 131727857HCID 131727857, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R)-2-{(4-[(Isopropylsulfonyl)amino]phenyl propanamide (1) (500 mg, 1.85 mmol) was dissolved in CH3OH (15 mL). NORMEX 1N NaOH (1.85 mL, 1.85 mmol) was added by dripping and the resulting solution was left stirring at room temperature for 2 h. After solvent evaporation, water (3 mL) was added and the clear solution was frozen and then lyophilized to give (2R)-2-{4-[(isopropylsulfonyl]amino}phenyl)propanamide sodium salt (541 mg, 1.85 mmol) as pale yellow powder. Quantitative yield. [α]D25 (c=0.4, CH3OH): −11.75°; 1H-NMR (D2O) δ 7.32 (d, 2H, J=7 Hz), 7.15 (d, 2H, J=7 Hz), 3.82 (q, 1H, J=7 Hz), 3.35 (m, 1H), 1.54 (d, 3H, J=7 Hz), 1.35 (d, 6H, J=7 Hz).

Workup

  1. waitthe resulting solution was left
  2. customAfter solvent evaporation, water (3 mL)
  3. additionwas added
  4. temperaturethe clear solution was frozen

Sources & evidence

ORD record
ord-edbf4f24e332452fbc0c9f352cbb600e
Source dataset
uspto-grants-2010_01
Patent number
US07652169B2

Reaction notes

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