Triethylamine → HCID 69731788, compound

HRID 23579Notes

Reaction equation

HRID 23579 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][NH:15][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69731619HCID 69731619, compound

Product 1

HCID 69731788HCID 69731788, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-aminomethyl-phenyl)-pent-4-enoic acid methyl ester (1.67 g, 6.55 mmol) in dichloromethane (50 cm3) at ambient temperature under an atmosphere of dry nitrogen was added triethylamine (4.56 cm3, 32.8 mmol) followed by dropwise addition of methanesulfonyl chloride (1.52 cm3, 19.7 mmol) over 5 minutes. The mixture was stirred for 4 hours at ambient temperature and the filtrate volatile fractions removed in vacuo to afford a crude yellow oil. The oil was dissolved in ethyl acetate (100 cm3), washed with saturated sodium bicarbonate (2×50 cm3), brine (25 cm3), dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to a crude yellow oil. The oil was purified by column chromatography (silica, eluting with hexane-ethyl acetate 4:1 to 1:1) to afford the title compound as a pale yellow viscous oil (1.85 g, 100%) with a positive ion ESI (M+H)+296.2.

Workup

  1. customthe filtrate volatile fractions removed in vacuo
  2. customto afford a crude yellow oil
  3. washwashed with saturated sodium bicarbonate (2×50 cm3), brine (25 cm3)
  4. dry with materialdried over sodium sulfate, vacuum
  5. filtrationfiltered
  6. customthe filtrate volatile fractions removed in vacuo to a crude yellow oil
  7. customThe oil was purified by column chromatography (silica, eluting with hexane-ethyl acetate 4:1 to 1:1)

Sources & evidence

ORD record
ord-615325f3dad0499da0a03de05a0d81ff
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

Loading…