tert-butyl N-(4-aminobutyl)carbamate → Tert-butyl[4-(methanesulfonylamino)butyl]carbamate

HRID 540856Notes

Reaction equation

HRID 540856 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(O)(=O)C>[C:9]([O:8][C:7](=[O:13])[NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:22]([CH3:21])(=[O:24])=[O:23])([CH3:10])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 54180899Tert-butyl[4-(methanesulfonylamino)butyl]carbamateYield 96.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere, a solution of tert-butyl N-(4-aminobutyl)carbamate (13.8 g, 73.4 mmol) and triethylamine (15.3 mL, 110 mmol) was cooled to 0° C. Methanesulfonyl chloride (6.3 mL, 81 mmol) was added, and the reaction was allowed to warm to ambient temperature and stirred overnight. Aqueous acetic acid (200 mL of 10%) was added. The organic layer was then separated and washed with water (200 mL), saturated aqueous sodium bicarbonate (200 mL), water (200 mL), and brine; dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 18.9 g of tert-butyl[4-(methanesulfonylamino)butyl]carbamate as an off-white solid.

Workup

  1. customThe organic layer was then separated
  2. washwashed with water (200 mL), saturated aqueous sodium bicarbonate (200 mL), water (200 mL), and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-234abd4122134a918ea109f9fcf648ed
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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