4-Fluorobenzenesulfonyl chloride → HCID 21697167, compound

HRID 1858967Notes

Reaction equation

HRID 1858967 reaction equation
Cl.[CH2:2]([NH:6][CH2:7][C:8]([O:10]CC)=[O:9])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].[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+]>Cl.O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:6]([CH2:7][C:8]([OH:10])=[O:9])[CH2:2][CH:3]([CH3:4])[CH3:5])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide2×HCID 857809383182-88-5

Product 1

HCID 21697167HCID 21697167, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A mixture of isobutylamino-acetic acid, ethyl ester hydrochloride (0.359 g, 0.00183 mol) in 6 M hydrochloric acid (10 mL) was refluxed for 20 hours and allowed to cool. The mixture was made basic with 50% wt/wt sodium hydroxide and 1 M sodium hydroxide to pH=5, and the volatiles were rotary evaporated. The residue was triturated 3 times with boiling methanol, and the triturates were combined and rotary evaporated. The residue was triturated 3 times with hot acetic acid, and the triturates were combined and rotary evaporated. The residue was dissolved in water and freeze-dried to give a white solid. This solid was combined with 4-fluoro-benzenesulfonyl chloride (0.3334 g, 0.001713 mol) and sodium carbonate (0.547 g, 0.00516 mol) in water, and the mixture was stirred at room temperature for 3 days. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was dried (MgSO4) and rotary evaporated to a white solid. The solid was chromatographed on silica gel (15 g, 230-400 mesh) eluting with dichloromethane-methanol (10:1, 10×15 mL). Fractions containing product were combined and rotary evaporated to give a white solid. The solid was dried in vacuo; yield 0.32 g (64% overall). 1H-NMR (DMSO-d6): δ7.85 (m, 2H), 7.39 (m, 2H), 3.91 (s, 2H), 3.32 (br s, H2O), 2.94 (d, 2H), 1.77 (m, 1H), 0.79 (d, 6H).

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureto cool
  3. customThe residue was triturated 3 times with boiling methanol
  4. customThe residue was triturated 3 times with hot acetic acid
  5. dissolutionThe residue was dissolved in water
  6. customfreeze-dried
  7. customto give a white solid
  8. extractionextracted with ethyl acetate
  9. dry with materialThe extract was dried (MgSO4)
  10. customrotary evaporated to a white solid
  11. customThe solid was chromatographed on silica gel (15 g, 230-400 mesh)
  12. washeluting with dichloromethane-methanol (10:1, 10×15 mL)
  13. additionFractions containing product
  14. customrotary evaporated
  15. customto give a white solid
  16. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-9707b12b10cd492ab4515195167de2d8
Source dataset
uspto-grants-2000_11
Patent number
US06153612

Reaction notes

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