Diisopropylethylamine → HCID 178486163, compound

HRID 1486596Notes

Reaction equation

HRID 1486596 reaction equation
[CH2:1]([C@H:8]1[CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:17])[S:13](Cl)(=[O:15])=[O:14].C(N(CC)C(C)C)(C)C>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:1]([CH:8]1[CH2:10][N@@:9]1[S:13]([N:12]([CH3:17])[CH3:11])(=[O:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 11062438(s)-2-benzylaziridine

Product 1

HCID 178486163HCID 178486163, compound

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

To a cooled (−10° C.) solution of (S)-2-benzylaziridine (100 g, 0.751 mol) and N,N-dimethylsulfamoyl chloride (84.5 mL, 0.787 mol) dichloromethane (100 mL) was added N,N-diisopropylethylamine (131 mL, 0.751 mol). The resulting yellow solution was stirred at −10° C. for a minimum of 16 hours. After this period, a 0.5M solution of citric acid (500 mL) was added and the phases were separated. The organic phase was then washed with 1.0 M sodium bicarbonate solution (500 mL). The organic phase was then solvent exchanged into tert-butyl methyl ether (500 mL). The solution was then cooled to 0° C., and heptane (100 mL) was added dropwise over a period of 2 hours. The mixture was then aged for an additional 2 hours at 0° C., and then cooled (−10° C.), to allowed compound IIa to precipitate out as a white, crystalline solid (27.8 g, 77%). Tlc assay: Rf 0.53 (SiO2; 1:1 heptane:ethyl acetate. KMnO4). 1H NMR (400 MHz, CDCl1): δ 7.20-7.29 (m, 5H), 2.94 (dd, J=14, 5 Hz, 1H), 2.80-2.88 (m, 1H), 2.70 (dd, J=14, 7 Hz, 1H), 2.66 (s, 6H), 2.56 (d, J=7 Hz, 1H), 2.14 (d, J=4 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ 137.4, 129.3, 128.9, 127.2, 40.6, 38.3, 38.1, 33.0.

Workup

  1. waitAfter this period
  2. customthe phases were separated
  3. washThe organic phase was then washed with 1.0 M sodium bicarbonate solution (500 mL)
  4. temperatureThe solution was then cooled to 0° C.
  5. additionheptane (100 mL) was added dropwise over a period of 2 hours
  6. waitThe mixture was then aged for an additional 2 hours at 0° C.
  7. temperaturecooled (−10° C.)
  8. customto precipitate out as a white, crystalline solid (27.8 g, 77%)

Sources & evidence

ORD record
ord-0d3158348f8b47c98bb989a7cb07dc40
Source dataset
uspto-grants-2016_08
Patent number
US09428473B2

Reaction notes

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