Triethylamine → tert-Butyl methylsulfonylcarbamate

HRID 711996Notes

Reaction equation

HRID 711996 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([O:15]C(OC(C)(C)C)=O)=O)([CH3:11])([CH3:10])[CH3:9].[CH3:23][S:24]([NH2:27])(=[O:26])=[O:25]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:23][S:24]([NH:27][C:13](=[O:15])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 72879MethanesulfonamideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 10081367tert-Butyl methylsulfonylcarbamateYield 64.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.2 mL, 16 mmol), di-tert-butyldicarbonate (2.65 g, 12.1 mmol) and 4-dimethylaminopyridine (0.096 g, 0.79 mmol) were added sequentially to a solution of methanesulfonamide (0.75 g, 7.9 mmol) in methylene chloride (20 mL) at room temperature. The reaction was stirred at room temperature for 2 h and then concentrated. EtOAc was added, and the resultant mixture was washed with 1N aq. HCl solution, dried over MgSO4 and concentrated to give the desired product (1 g) to be used in the next step directly.

Workup

  1. concentrationconcentrated
  2. additionEtOAc was added
  3. washthe resultant mixture was washed with 1N aq. HCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-836d82747f414104877ffad99140d64a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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