Acetyl chloride → N-({8-Benzyl-7-[2,4-dioxo-3-azabicyclo[3.1.0]hex-3-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}methyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82857Notes

Reaction equation

HRID 82857 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][NH:19][S:20]([C:23]3[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=3)(=[O:22])=[O:21])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:29][C:30]([C@H:32]1[CH2:34][C@H:33]1[C:35](O)=[O:36])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C>O1CCCC1.O>[CH2:1]([CH:8]1[C:17]2[CH:16]=[C:15]([CH2:18][NH:19][S:20]([C:23]3[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=3)(=[O:21])=[O:22])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH:9]1[N:29]1[C:35](=[O:36])[CH:33]2[CH:32]([CH2:34]2)[C:30]1=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 86685675cis-2-{[1-Benzyl-7-({[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}methyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl}cyclopropanecarboxylic acid

Product 1

HCID 86685674N-({8-Benzyl-7-[2,4-dioxo-3-azabicyclo[3.1.0]hex-3-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}methyl)-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

cis-2-{[1-Benzyl-7-({[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}methyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl}cyclopropanecarboxylic acid (382 mg, 0.731 mmol) was dissolved in tetrahydrofuran (10 mL) and acetyl chloride (5 mL, 88 mmol) was added. The reaction mixture was heated under reflux for 2 h. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic extracts were washed with aqueous sodium bicarbonate solution, dried (sodium sulfate) and concentrated in vacuo. The crude product was used for the next step without further purificiation. Yield: 377 mg (light orange oil).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts were washed with aqueous sodium bicarbonate solution
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f148f1807654e248729cd5dd330c8fa
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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