Water → HCID 86729742, compound

HRID 2272581Notes

Reaction equation

HRID 2272581 reaction equation
[NH2:1][CH2:2][CH:3]([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)#[N:15].O>C1COCC1>[C:14]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:1][CH2:2][CH:3]([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])(=[O:24])=[O:23])=[CH:20][CH:21]=1)#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 394974-Cyanobenzenesulfonyl chlorideHCID 44629801tert-Butyl (3-amino-2-methylpropyl)carbamate

Product 1

HCID 86729742HCID 86729742, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3-amino-2-methylpropyl)carbamate (200 mg, 1.06 mmol) and TEA (0.444 mL, 3.19 mmol) in THF (5 mL) was added 4-cyanobenzene-1-sulfonyl chloride (214 mg, 1.06 mmol), and the mixture was stirred at room temperature for 16 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give tert-butyl (3-(4-cyanophenylsulfonamido)-2-methylpropyl)carbamate (273 mg, 0.772 mmol, 72.7%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a4e7fa5f657c424095588604b4b8dabb
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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