p-Toluenesulfonic acid monohydrate → HCID 86604793, compound

HRID 132223Notes

Reaction equation

HRID 132223 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[C:19](=O)[C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[N:16](COCC[Si](C)(C)C)[S:15]2(=[O:34])=[O:33])[CH2:10][CH2:9]1)=O)(C)(C)C.[BH4-].[Na+].O.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1>CO>[C:38]1([CH3:48])[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1.[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15](=[O:33])(=[O:34])[NH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydrideHCID 59731890HCID 59731890, compound

Product 1

HCID 86604793HCID 86604793, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-[2,2,4-Trioxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2,3,4-tetrahydro-2λ6-2,1-benzothiazin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester (865 mg, 1.7 mmol) was dissolved in methanol (25 mL). Mixture was cooled to 0° C. Sodium borohydride (100 mg, 2.6 mmol) was added to the mixture in three portions. Reaction stirred at 0° C. for 3 hours. Mixture was concentrated by roto-vap. Residue was treated with 1N hydrochloric acid. Material was extracted twice with ethyl acetate. Organic phase was dried (magnesium sulfate), filtered and concentrated to dryness. Residue was dissolved in benzene (20 mL). p-Toluenesulfonic acid monohydrate (475 mg, 2.5 mmol) was added to the mixture. Reaction was heated to reflux and held with stirring for 1 hour. Mixture was cooled to room temperature. Solids were filtered off. The sticky solid was treated with hot isopropyl alcohol (10 mL). Mixture was cooled to room temperature and allowed to stand overnight. Solids were filtered off, washed with isopropyl alcohol and then dried under high vacuum. Title compound was obtained as tan solid in 65% yield. MS m/e (M+H)+=265.2.

Workup

  1. customReaction
  2. concentrationMixture was concentrated by roto-vap
  3. additionResidue was treated with 1N hydrochloric acid
  4. extractionMaterial was extracted twice with ethyl acetate
  5. dry with materialOrganic phase was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. dissolutionResidue was dissolved in benzene (20 mL)
  9. customReaction
  10. temperaturewas heated
  11. temperatureto reflux
  12. stirringwith stirring for 1 hour
  13. temperatureMixture was cooled to room temperature
  14. filtrationSolids were filtered off
  15. additionThe sticky solid was treated with hot isopropyl alcohol (10 mL)
  16. temperatureMixture was cooled to room temperature
  17. waitto stand overnight
  18. filtrationSolids were filtered off
  19. washwashed with isopropyl alcohol
  20. customdried under high vacuum

Sources & evidence

ORD record
ord-01499433f4fa4b0096a7371f7ebbefa9
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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