Sodium Hydroxide → HCID 131727857, compound

HRID 252310Notes

Reaction equation

HRID 252310 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-ba33bd32646c417db0f599635ad5209c
Source dataset
uspto-grants-2011_01
Patent number
US07868046B2

Reaction notes

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