Hydrochloric Acid → HCID 22711519, compound

HRID 352979Notes

Reaction equation

HRID 352979 reaction equation
C(O[C:6]([CH:8]1[NH:13][CH2:12][C:11]2[O:14][C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([S:25]([C:28]4[NH:29][C:30]5[C:35]([CH:36]=4)=[CH:34][C:33]([Cl:37])=[CH:32][CH:31]=5)(=[O:27])=[O:26])[CH2:21][CH2:20]3)=[O:18])=[N:16][C:10]=2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.Cl.O1CCCC1>C(Cl)Cl.CO>[ClH:37].[Cl:37][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([S:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17]([C:15]3[O:14][C:11]4[CH2:12][NH:13][CH:8]([CH3:6])[CH2:9][C:10]=4[N:16]=3)=[O:18])[CH2:20][CH2:21]1)(=[O:27])=[O:26])=[CH:36]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 22710043HCID 22710043, compound

Product 1

HCID 22711519HCID 22711519, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[[6-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridin-2-yl]carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine (100 mg) in methylene chloride (3.0 ml) was added trifluoroacetic acid (3.0 ml) at room temperature, followed by stirring for 15 minutes. The reaction mixture was concentrated under reduced pressure. To the residue were added methylene chloride (4.0 ml), triethylamine (50.0 μl), acetic acid (21.0 μl), formalin (23.5 μl) and sodium triacetoxyborohydride (58.0 mg) at room temperature. After stirring for 1 hour, methylene chloride (20 ml) and a saturated aqueous solution (50 ml) of sodium bicarbonate were added to the reaction mixture to separate it into layers. The water layer was extracted with methylene chloride (20 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by preparative thin-layer chromatography (chloroform : methanol=10:1) using silica gel, whereby the free form (82.6 mg) of the title compound was obtained as a colorless solid. To the resulting compound were added a 1N aqueous solution of hydrochloric acid, tetrahydrofuran and methanol, followed by concentration under reduced pressure, whereby the title compound was obtained as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue were added methylene chloride (4.0 ml), triethylamine (50.0 μl), acetic acid (21.0 μl), formalin (23.5 μl) and sodium triacetoxyborohydride (58.0 mg) at room temperature
  3. stirringAfter stirring for 1 hour
  4. additionmethylene chloride (20 ml) and a saturated aqueous solution (50 ml) of sodium bicarbonate were added to the reaction mixture
  5. customto separate it into layers
  6. extractionThe water layer was extracted with methylene chloride (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by preparative thin-layer chromatography (chloroform : methanol=10:1)
  11. customwas obtained as a colorless solid
  12. concentrationfollowed by concentration under reduced pressure, whereby the title compound
  13. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-9cf7a427ad974387bf60e6aef9e463d8
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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