Diisopropylethylamine → benzyl N-(2-oxoethyl)carbamate

HRID 1183134Notes

Reaction equation

HRID 1183134 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CS(C)=O>[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 280458benzyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 11217768benzyl N-(2-oxoethyl)carbamateYield 82.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (2-hydroxyethyl)carbamic acid benzyl ester (1.0 g, 5.1 mmol) and DIPEA (1.78 mL, 10.2 mmol) in DCM (15 mL) was added a solution of sulfur trioxide-pyridine complex (1.63 g, 10.2 mmol) in DMSO (15 mL) at −20° C. After 1 h, the reaction was warmed to room temperature, diluted with dichloromethane (50 mL) and washed with 1.0 N HCl (50 mL) and brine. The organics were separated, dried with anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel chromatography to give the title intermediate (810 mg, 82%). 1H NMR (CDCl3, 300 MHz) δ (ppm): 9.5 (s, 1H) 7.4-7.2 (m, 5H), 5.1 (s, 2H), 3.9 (d, J=5.8 Hz, 2H), 2.9-3.3 (br, 1H).

Workup

  1. washwashed with 1.0 N HCl (50 mL) and brine
  2. customThe organics were separated
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a23335730a844815ab3afea0688add57
Source dataset
uspto-grants-2014_03
Patent number
US08664242B2

Reaction notes

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