Triethylamine → HCID 19034092, compound

HRID 265860Notes

Reaction equation

HRID 265860 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH2:14]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH2:20])[CH3:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:17]([CH2:18][CH2:19][NH:20][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])([O:16][CH2:14][CH3:15])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 419889Ethyl 3-aminopropanoate

Product 1

HCID 19034092HCID 19034092, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-chlorosulfonylbenzoic acid (3-1) (Maybridge Chemicals) (1.10 g, 5 mmoles) and β-alanine ethyl ester (0.85 g, 5.5 mmoles) in CHCl3 (20 ml) at room temperature was added triethylamine (1.52 g, 15 mmoles). After stirring for 3 hrs the solvent was removed, the residue was taken up in EtOAc, washed with H2O, 10% KHSO4 solution, H2O, brine and dried (Na2SO4). Solvent removal gave a residue that was purified by flash chromatography on silica gel eluting with CHCl3 (97)/MeOH(3) to give pure 3-2.

Workup

  1. customwas removed
  2. washwashed with H2O, 10% KHSO4 solution, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent removal
  5. customgave a residue that
  6. customwas purified by flash chromatography on silica gel eluting with CHCl3 (97)/MeOH(3)
  7. customto give pure 3-2

Sources & evidence

ORD record
ord-4b4a230632b54cb482997d534908a6c6
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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