Hydrochloric Acid → HCID 11596180, compound

HRID 870347Notes

Reaction equation

HRID 870347 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH:19]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:18][CH2:17]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:23]=[CH:22][C:21]3[CH2:20][C@H:19]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:17][C:16]=3[CH:15]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68916821HCID 68916821, compound

Product 1

HCID 11596180HCID 11596180, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[6-(4-Isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propionamide (0.19 g, 0.47 mmol) was dissolved in 10 mL of tetrahydrofuran (THF) and 3 mL (31.3 mmol) of a borane-THF complex was introduced dropwise over 20 min. The resulting mixture was stirred at reflux for 3 h. The solution was cooled, 3 mL of 2 N HCl was added slowly, and the mixture was stirred at 40° C. for 1 h. The cooled solution was quenched with water, then NaOH (2N) and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and the filtrate was evaporated in vacuo to give the product as a colorless oil (100 mg, 55%).

Workup

  1. addition3 mL (31.3 mmol) of a borane-THF complex was introduced dropwise over 20 min
  2. temperatureat reflux for 3 h
  3. temperatureThe solution was cooled
  4. stirringthe mixture was stirred at 40° C. for 1 h
  5. customThe cooled solution was quenched with water
  6. extractionNaOH (2N) and extracted with ethyl acetate
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8a39beaac24d46b6b510ba35eaf76bfc
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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