Pyridine → HCID 67213765, compound

HRID 2421616Notes

Reaction equation

HRID 2421616 reaction equation
N1C=CC=CC=1.[C:7]([NH:14][CH2:15][CH2:16]O)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>CCOCC>[C:7]([NH:14][CH2:15][CH2:16][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 67213765HCID 67213765, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Pyridine (1.5 mL, 18.5 mmol) was added to 2-(N-Boc-amino)-ethanol (280 mg, 1.7 mmol) at 0° C. Tosyl chloride (1.65 g, 8.7 mmol) was then added and the reaction was allowed to stir at 0° C. overnight. The resulting cloudy reaction was diluted with Et2O and washed with water, saturated NaHCO3 and brine, dried over MgSO4 and concentrated. The resulting white solid was purified using SiO2 with AcOEt/petroleum ether 20:80 to 30:70. A white solid was obtained (250 mg, 46%). NMR 1H (ppm, CDCl3): 7.77 (d, J3=8.3 Hz, 2H), 7.33 (d, J3=8.0 Hz, 2H), 4.82 (br. s., 1H), 4.05 (t, J3=5.08 Hz, 2H), 3.38-3.33 (m, 2H), 2.43 (s, 3H), 1.39 (s, 9H).

Workup

  1. customThe resulting cloudy reaction
  2. washwashed with water, saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting white solid was purified
  6. customA white solid was obtained (250 mg, 46%)

Sources & evidence

ORD record
ord-05345e48212f48328830eeccdfd3e35e
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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