4-Toluenesulfonyl chloride → tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate

HRID 1778013Notes

Reaction equation

HRID 1778013 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 10781634tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of tert-butyl(2-hydroxyethyl)carbamate (0.960 mL, 6.08 mmol) in pyridine (25 ml) was added 4-methylbenzene-1-sulfonyl chloride (2.341 g, 12.16 mmol) at −10° C. The solution was stirred at −10° C. for 40 min. The reaction mixture was stored in a fridge at 4° C. for 4 days. It was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed aqueous citric acid (10%), dried using MgSO4, filtered and evaporated to give the title compound as a yellow oil. (UPLC-MS 3) ESI-MS 316.2 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 7.79 (d, 2H), 7.36 (d, 2H), 4.84 (s, 1H), 4.06 (t, 2H), 3.41-3.35 (m, 2H), 2.45 (s, 3H), 1.40 (s, 9H).

Workup

  1. waitThe reaction mixture was stored in a fridge at 4° C. for 4 days
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed aqueous citric acid (10%)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e896ba64205c43b59c81d30ed0dd3a44
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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