Triethylamine → tert-Butyl 6-{[(2-nitrophenyl)sulfonyl]amino}hexylcarbamate

HRID 1936598Notes

Reaction equation

HRID 1936598 reaction equation
Cl.[C:2]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].C(N(CC)CC)C.[N+:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34])([O-:26])=[O:25]>C(Cl)Cl>[C:5]([O:4][C:2](=[O:3])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N+:24]([O-:26])=[O:25])(=[O:34])=[O:35])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 3017638tert-Butyl (6-aminohexyl)carbamate monohydrochloride

Product 1

HCID 53921292tert-Butyl 6-{[(2-nitrophenyl)sulfonyl]amino}hexylcarbamateYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-Boc 1,6-diaminohexane hydrochloride(1.51 g, 6 mmol) and triethyl amine(1.31 g, 13 mmol) in 50 mL methylene chloride was added 2-Nitrobenzenesulfonyl chloride(1.326 g, 6 mmol). The reaction mixture was stirred for 6 h at room temperature, quenched with brine, and extracted with methylene chloride(2×50 mL). The organic layer was washed with brine (a saturated solution of sodium chloride in water, unless otherwise specified), dried over anhydrous sodium sulfate, and concentrated in vacuo to yield the titled compound as yellow oil(2.1 g, 87%).

Workup

  1. customquenched with brine
  2. extractionextracted with methylene chloride(2×50 mL)
  3. washThe organic layer was washed with brine (a saturated solution of sodium chloride in water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06c95ac8cb7a48639501777c227ab2a3
Source dataset
uspto-grants-2002_05
Patent number
US06391877B1

Reaction notes

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