Ethylamine → HCID 53990869, compound

HRID 1081283Notes

Reaction equation

HRID 1081283 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[S:17][C:16]2[S:15](=[O:19])(=[O:18])[NH:14][CH2:13][C:12](=O)[C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.C1(C)C=CC(S(Cl)(=O)=[O:35])=CC=1.C(N)C.[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>>[CH2:44]([O:45][C:46](=[O:35])[CH2:42][CH2:12][CH2:13][N:14]1[CH2:27][C@H:26]([NH:23][CH2:24][CH3:25])[C:11]2[CH:10]=[C:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[S:17][C:16]=2[S:15]1(=[O:18])=[O:19])[CH3:43]

Participants

6

Reactant 5

HCID 6341EthylamineHCID 73974-Toluenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 23363812HCID 23363812, compound

Product 1

HCID 53990869HCID 53990869, compoundYield 37.6%

Conditions

Temperature
0 °C

Procedure

The product of Step A (8.50g, 19.07 mmol) was dissolved in THF (130 mL) and cooled to 0° C. Triethylamine (10.69 mL, 76.28 mmol) was added followed by p-toluenesulfonyl chloride. The mixture was stirred for three hours and an aqueous solution of ethylamine (20 mL) was added. The mixture was stirred overnight at room temperature and then evaporated to a residue which was diluted with ethyl acetate (100 mL). The ethyl acetate was separated, dried (MgSO4) and evaporated to provide a brown residue which was purified by column chromatography (silica, hexane-ethyl acetate gradient) to give 3.5 g (37.6%) of the desired compound as an oil.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customevaporated to a residue which
  3. additionwas diluted with ethyl acetate (100 mL)
  4. customThe ethyl acetate was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto provide a brown residue which
  8. customwas purified by column chromatography (silica, hexane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-45f40a28d0d44f4185d5f8f36452df81
Source dataset
uspto-grants-1996_12
Patent number
US05585377

Reaction notes

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