Citric Acid → HCID 15298701, compound

HRID 274236Notes

Reaction equation

HRID 274236 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:11])[CH2:6][NH:7]CC#C)[CH3:3].C(N([CH:18]([CH3:20])[CH3:19])CC)(C)C.[CH2:21]([S:25](Cl)(=[O:27])=[O:26])[CH2:22][CH2:23][CH3:24].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCOCC>[CH2:21]([S:25]([NH:7][CH:6]([CH2:20][C:18]#[CH:19])[C:5]([O:4][CH2:2][CH3:3])=[O:11])(=[O:27])=[O:26])[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 754301-Butanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86748458HCID 86748458, compound

Product 1

HCID 15298701HCID 15298701, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of propargyl glycine ethyl ester hydrochloride (from treatment of 2.0 g (17.7 mmol) with EtOH/HCl at reflux) in CH2Cl12 (30 μl) and 10 ml (57 mmol) diisopropylethylamine was cooled to 0° C. and 35 ml of butanesulfonyl chloride added dropwise. After 30 minutes, reaction mixture was poured into the cold 10% citric acid solution and saturated with ether. The organic phase was washed with NaHCO3 solution, brine and dried (MgSO4). The crude product was purified by flash column chromatography to afford 2.6 g of 18-1.

Workup

  1. customreaction mixture
  2. washThe organic phase was washed with NaHCO3 solution, brine
  3. dry with materialdried (MgSO4)
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-1170e69ca2fc49cd954f708ff5f10696
Source dataset
uspto-grants-1995_02
Patent number
US05389631

Reaction notes

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