Hydrochloric Acid → HCID 22999705, compound

HRID 1935426Notes

Reaction equation

HRID 1935426 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12](C(OC(C)(C)C)=O)=[C:11]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[O:10][N:9]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].Cl>ClCCl.C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:28][CH:29]=2)(=[O:22])=[O:23])[O:10][N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22999719HCID 22999719, compound

Product 1

HCID 22999705HCID 22999705, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[2-(acetoxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-isoxazolecarboxylate (Preparation 2) (3.16 g) in dichloromethane (40 mL) was added trifluoroacetic acid (20 mL). The reaction mixture was heated to reflux for 3 hours. After which time the reaction mixture was basified to pH8 using sodium hydrogen carbonate solution and then re-acidified to pH2 using aqueous hydrochloric acid (1.0 M). This aqueous layer was extracted into ethyl acetate (2×250 mL) and the organics combined, dried over magnesium sulfate and the solvent removed in vacuo to yield the crude material (2.6 g). This was dissolved up in toluene and refluxed for 2 hours. The solvent was removed in vacuo to yield the crude material as a light brown solid (2.3 g). The crude material was purified using the Biotage Flash 40i system (silica, 90 g) and eluted with hexane:ethyl acetate (5:2) to yield the product as a white solid (1.2 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionThis aqueous layer was extracted into ethyl acetate (2×250 mL)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customto yield the crude material (2.6 g)
  7. temperaturerefluxed for 2 hours
  8. customThe solvent was removed in vacuo
  9. customto yield the crude material as a light brown solid (2.3 g)
  10. customThe crude material was purified
  11. washeluted with hexane:ethyl acetate (5:2)

Sources & evidence

ORD record
ord-bbe99d703fcc4d93afd8eea3f8dc9496
Source dataset
uspto-grants-2002_05
Patent number
US06387915B2

Reaction notes

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