Hydrochloric Acid → HCID 68920278, compound

HRID 870348Notes

Reaction equation

HRID 870348 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH2:17][C@@H:18]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:19]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:15]3[CH2:16][CH2:17][C@@H:18]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:19][C:20]=3[CH:21]=[CH:22][CH:23]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68913979HCID 68913979, compound

Product 1

HCID 68920278HCID 68920278, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)—N-[5-(4-Isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propionamide (0.48 g, 1.20 mmol) was dissolved in 10 mL of THF and 5 mL (8.36 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, 5 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 (130 mg, 28%).

Workup

  1. addition5 mL (8.36 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-732f5dd904c9402491c1d597410cface
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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