Ethylamine → HCID 22901960, compound

HRID 1489819Notes

Reaction equation

HRID 1489819 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH:31](O)[C:30]3[CH:34]=[C:35]([S:37]([NH2:40])(=[O:39])=[O:38])[S:36][C:29]=3[S:28]2(=[O:42])=[O:41])=[CH:23][CH:22]=1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:43]([N:45](CC)CC)[CH3:44].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N)C>C1COCC1>[CH2:43]([NH:45][CH:31]1[C:30]2[CH:34]=[C:35]([S:37]([NH2:40])(=[O:39])=[O:38])[S:36][C:29]=2[S:28](=[O:41])(=[O:42])[N:27]([C:24]2[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][O:1][Si:2]([C:15]([CH3:16])([CH3:18])[CH3:17])([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:22][CH:23]=2)[CH2:32]1)[CH3:44]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22901933HCID 22901933, compound

Product 1

HCID 22901960HCID 22901960, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

The product from Step D (1.77 g, 2.75 mmol) was dissolved in dry THF (15 mL) containing triethylamine (1.54 mL, 11 mmol) and cooled to 5° C. p-Toluenesulfonyl chloride (1.05 g, 5.5 mmol) was added and the mixture stirred at 5° C. for 4.5 hr. An excess of ethylamine was condensed into the reaction mixture which was stirred at ambient temperature for 18 hr and then evaporated to dryness. The residue was suspended in water and this mixture was extracted with ethyl acetate (2×50 mL). the combined extracts were dried (NaSO4) and purified by column chromatography (silica, 3.5% ethanol/methylene chloride) to provide 0.8 g (44%) of a solid: mp 66° C.

Workup

  1. additionwas added
  2. customcondensed into the reaction mixture which
  3. stirringwas stirred at ambient temperature for 18 hr
  4. customevaporated to dryness
  5. extractionthis mixture was extracted with ethyl acetate (2×50 mL)
  6. dry with materialthe combined extracts were dried (NaSO4)
  7. custompurified by column chromatography (silica, 3.5% ethanol/methylene chloride)

Sources & evidence

ORD record
ord-3852c9e86bed49b18d81e98684e5ae31
Source dataset
uspto-grants-1997_10
Patent number
US05679670

Reaction notes

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