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

HRID 1173061Notes

Reaction equation

HRID 1173061 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][N:11]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:12]3)=[CH:4][CH:3]=1.[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20].C(N(CC)CC)C>O1CCCC1>[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]3[CH2:14][C@@H:13]4[C@H:9]3[CH2:10][N:11]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:12]4)=[CH:6][CH:7]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 673664421-[(1R,5S,6R)-6-(4-aminophenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-propan-1-one

Product 1

HCID 673660504-Isopropyl-N-[4-((1R,5S,6R)-3-propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamideYield 113.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.935 g of 1-((1R,5S,6R)-6-(4-amino-phenyl)-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one (3.83 mmol) were dissolved in 30 ml of tetrahydrofuran and 0.795 g of 4-isopropylbenzenesulfonyl chloride (3.64 mmol) and 1.6 ml of triethylamine (11.48 mmol) were added. After stirring for 18 h at room temperature, the solvent was evaporated under reduced pressure, the remaining material was partitioned between diethyl ether and water that was adjusted to alkaline pH with 1 N aqueous sodium hydroxide. The aqueous layer was reextracted three times with diethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated to yield 1.76 g of crude product that was used in the subsequent reaction step without further purification.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe remaining material was partitioned between diethyl ether and water that
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-092ca0ddbc774f70b49c60cf46acef0b
Source dataset
uspto-grants-2010_11
Patent number
US07834048B2

Reaction notes

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