Water → tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamate

HRID 2402236Notes

Reaction equation

HRID 2402236 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>ClCCl>[CH3:19][S:20]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 187201N-BOC-ethylenediamine

Product 1

HCID 47454467tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(2-Aminoethyl)(tert-butoxy)carboxamide (17.5 mL, 0.11 mol) [Alfa #L19947] was stirred in dichloromethane (320 mL) and triethylamine (33 mL, 0.24 mol) was added. A solution of methanesulfonyl chloride (8.5 mL, 0.11 mol) in dichloromethane (10 mL) was added. The resulting mixture was stirred for 1 hour and water (30 mL) was added. The product was extracted with dichloromethane (3×30 mL), dried over sodium sulfate and concentrated in vacuo to give the desired product (21 g, 81%). LCMS calculated for C3H11N2O2S (M-Boc+H)+: m/z=139.1.

Workup

  1. extractionThe product was extracted with dichloromethane (3×30 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4a908d74fb143ce8c51dcd03b9e0985
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

Loading…