2-(3-Thienyl)-1,3-dioxolane → N-[[3-(1,3-dioxolan-2-yl)-2-thienyl]sulfonyl]glycine ethyl ester

HRID 1736007Notes

Reaction equation

HRID 1736007 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11](Cl)(=[O:13])=[O:12].C1OC(C2C=CSC=2)OC1.Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27]>C(=O)(O)[O-].[Na+]>[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH:31][S:11]([C:7]1[S:8][CH:9]=[CH:10][C:6]=1[CH:2]1[O:3][CH2:4][CH2:5][O:1]1)(=[O:13])=[O:12])[CH3:27]

Participants

5

Reactant 3

HCID 3156302-(3-Thienyl)-1,3-dioxolaneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 105389153-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl Chloride

Product 1

HCID 21480494N-[[3-(1,3-dioxolan-2-yl)-2-thienyl]sulfonyl]glycine ethyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-(1,3-dioxolan-2-yl)-thiophene-2-sulfonyl chloride, prepared from thiophene-3-carboxaldehyde ethylene acetal (13.27 g, 85.1 mmol) as described in Example 6, Step A, was combined with glycine ethyl ester hydrochloride (33.99 g, 221 mmol) and a saturated aqueous solution of sodium bicarbonate (250 mL). After stirring for 18 hr at ambient temperature, the organic layer was separated, dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 40% ethyl acetate/hexane) to give an oil (16.55 g, 61%).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated to a residue which
  4. customwas purified by column chromatography (silica, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f8a3d037be1946a293f886ac332b0ec8
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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