Hydrochloric Acid → 4-Isopropyl-N-[4-((1R,5S,6R)-3-propyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamide

HRID 1173062Notes

Reaction equation

HRID 1173062 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:26][C@@H:25]4[C@H:21]3[CH2:22][N:23]([C:27](=O)[CH2:28][CH3:29])[CH2:24]4)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>O1CCCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:26][C@@H:25]4[C@H:21]3[CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24]4)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 673660504-Isopropyl-N-[4-((1R,5S,6R)-3-propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 114952864-Isopropyl-N-[4-((1R,5S,6R)-3-propyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamideYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.9 g of 4-isopropyl-N-[4-((1R,5S,6R)-3-propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamide (2.11 mmol) were dissolved in tetrahydrofuran and 11 ml of a 1 M borane/THF complex in tetrahydrofuran (10.8 mmol) was added at room temperature. The reaction mixture was heated under reflux for 30 minutes, 10 ml of aqueous 2 N hydrochloric acid were added, and the mixture was again refluxed for 3 h. After cooling to room temperature, the solvent was evaporated, the residue was treated with 50% aqueous sodium hydroxide solution, and the aqueous layer was extracted twice with diethyl ether. The combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated to yield 0.824 g of crude product which was then purified via preparative HPLC (column Delta Pak, 40 mm diameter, methanol/water/0.1% acetic acid) to yield 0.078 g of the purified product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture was again refluxed for 3 h
  4. customthe solvent was evaporated
  5. additionthe residue was treated with 50% aqueous sodium hydroxide solution
  6. extractionthe aqueous layer was extracted twice with diethyl ether
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customto yield 0.824 g of crude product which
  11. customwas then purified via preparative HPLC (column Delta Pak, 40 mm diameter, methanol/water/0.1% acetic acid)

Sources & evidence

ORD record
ord-2b997e0e264a4727b5088ecbd5280091
Source dataset
uspto-grants-2010_11
Patent number
US07834048B2

Reaction notes

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