4-Toluenesulfonyl chloride → 2-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonate

HRID 1774655Notes

Reaction equation

HRID 1774655 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CCN(CC)CC.[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:27][C:26]1[CH:28]=[CH:29][C:23]([S:20]([O:1][CH2:2][CH2:3][N:4]([C:5]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:11])[CH3:12])(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 215811562-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 112a (9.0 g, 51 mmol), and Et3N (18.6 mL, 51 mmol) in DCM (100 mL) was added TsCl (9.77 g, 51 mmol). The mixture was stirred at rt for 4 h and concentrated. The residue was diluted with EA, washed with water. The organic layer was dried and concentrated to give 2-(tert-butoxycarbonyl(methyl)amino)ethyl 4-methylbenzenesulfonate 112b (10.0 g, 61%) as light yellow oil. ESI-LCMS: m/z=230.0

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EA
  3. washwashed with water
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b07a8d8a777041a68e7f3c4dec6599b4
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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