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

HRID 1581951Notes

Reaction equation

HRID 1581951 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-f9aa1e09d3da4c24b3cab615d9e4a42a
Source dataset
uspto-grants-2004_05
Patent number
US06734182B2

Reaction notes

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