Ethylamine → HCID 19737966, compound

HRID 2255510Notes

Reaction equation

HRID 2255510 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH:16](O)[C:15]2[CH:19]=[C:20]([S:22]([NH2:25])(=[O:24])=[O:23])[S:21][C:14]=2[S:13]1(=[O:27])=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:28]([N:30](CC)CC)[CH3:29].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N)C>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH:16]([NH:30][CH2:28][CH3:29])[C:15]2[CH:19]=[C:20]([S:22]([NH2:25])(=[O:24])=[O:23])[S:21][C:14]=2[S:13]1(=[O:27])=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 19737968HCID 19737968, compound

Product 1

HCID 19737966HCID 19737966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product of Step D (1.4 g , 3 mmol) and triethylamine (1.7 mL, 12 mmol) in THF (10 mL) at -20° C. was added p-toluenesulfonyl chloride (1.2 g, 6 mmol) and the reaction mixture was stirred at 0° C. for 5 hr. The reaction mixture was cooled to -78° C. at which point ethylamine (10 mL) was added; this mixture was allowed to warm to reflux temperature for 2 hr and then maintained at room temperature for 40 hr. After removing the solvent the crude product was diluted with ethyl acetate (150 mL), washed with water (2×50 mL) and brine (2×50 mL), dried (MgSO4), and evaporated to a syrup which was purified by column chromatography [silica; CH3OH/CH2Cl2 (20:1)] to give 900 mg (64%) as a colorless foam.

Workup

  1. additionwas added
  2. temperatureto warm
  3. temperatureto reflux temperature for 2 hr
  4. temperaturemaintained at room temperature for 40 hr
  5. customAfter removing the solvent the crude product
  6. additionwas diluted with ethyl acetate (150 mL)
  7. washwashed with water (2×50 mL) and brine (2×50 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated to a syrup which
  10. customwas purified by column chromatography [silica; CH3OH/CH2Cl2 (20:1)]
  11. customto give 900 mg (64%) as a colorless foam

Sources & evidence

ORD record
ord-570947357ce74572830151779f21af0b
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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