4-Fluorobenzenesulfonyl chloride → (+/-)-2-(4-Fluoro-benzenesulfonylamino)-5-phenyl pentanoic acid

HRID 378927Notes

Reaction equation

HRID 378927 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:1][CH:2]([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]([OH:5])=[O:4])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 2968662-Amino-5-phenylpentanoic acid

Product 1

HCID 21697171(+/-)-2-(4-Fluoro-benzenesulfonylamino)-5-phenyl pentanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (±)-2-amino-5-phenyl-pentanoic acid (0.188 g, 0.000973 mol), 4-fluoro-benzenesulfonyl chloride (0.189 g, 0.000971 mol), and sodium carbonate (0.208 g, 0.00196 mol) in water (4 mL) was stirred at room temperature for 4 days. The mixture was heated briefly on a steam bath to give a cloudy solution. The solution was gravity filtered hot, and the filtrate allowed to cool. The resulting solid that crystallized was filtered off, washed with water, and dried in vacuo; yield 0.131 g, (38%). 1H-NMR (DMSO-d6): δ7.81 (m, 2H), 7.37 (t, 2H), 7.25 (t, 2H), 7.14 (m, 4H), 3.34 (br s, H2), 3.04 (t, 1H), 2.46 (m, 2H), 1.6-1.4 (m, 4H).

Workup

  1. temperatureThe mixture was heated briefly on a steam bath
  2. customto give a cloudy solution
  3. filtrationfiltered hot
  4. temperatureto cool
  5. customThe resulting solid that crystallized
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5fb4fa50ee1e4ec49a7bb5f85520ae3f
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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