Hydrochloric Acid → HCID 21697167, compound

HRID 378931Notes

Reaction equation

HRID 378931 reaction equation
Cl.[CH2:2]([NH:6][CH2:7][C:8]([O:10]CC)=[O:9])[CH:3]([CH3:5])[CH3:4].Cl.[OH-].[Na+].[F:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:6]([CH2:7][C:8]([OH:10])=[O:9])[CH2:2][CH:3]([CH3:4])[CH3:5])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide2×HCID 857809383182-88-5

Product 1

HCID 21697167HCID 21697167, compound

Reagents, catalysts & solvents 1

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).

Workup

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

Sources & evidence

ORD record
ord-6f831d205cae4cf8b7cf5341fee23bc3
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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