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

HRID 1624235Notes

Reaction equation

HRID 1624235 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:12]([O:16][C:17](=[O:22])[NH:18][CH2:19][CH2:20][OH:21])([CH3:15])([CH3:14])[CH3:13].CCN(CC)CC>C(Cl)Cl>[C:12]([O:16][C:17]([NH:18][CH2:19][CH2:20][O:21][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])=[O:22])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 10781634tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tosyl chloride (1.50 g, 7.87 mmol) was added to a solution of (2-hydroxy-ethyl)-carbamic acid tert-butyl ester (0.84 g, 5.2 mmol) and Et3N (1.23 mL, 8.82 mmol) in CH2Cl2 (26 mL), and the solution was stirred at room temperature for 17 h. The solution was washed with H2O (15 mL), and the aqueous phase was extracted with CH2Cl2 (10 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (20% EtOAc/hexanes) gave yellow crystals (1.29 g, 79%). 1H NMR (CDCl3) δ 1.41 (s, 9H), 2.45 (s, 3H), 3.38 (m, 2H), 4.07 (m, 2H), 4.82 (br s, 1H), 7.35 (d, 2H, J=8.1 Hz), 7.79 (d, 2H, J=8.1 Hz).

Workup

  1. washThe solution was washed with H2O (15 mL)
  2. extractionthe aqueous phase was extracted with CH2Cl2 (10 mL)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude material by column chromatography on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bbc862dd559848828ba4b23435c5320d
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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