Hydrochloric Acid → N-[(3-formyl-thien-2-yl)sulfonyl]glycine ethyl ester

HRID 1490048Notes

Reaction equation

HRID 1490048 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][NH:6][S:7]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH:15]1OCC[O:16]1)(=[O:9])=[O:8])[CH3:2].Cl>C1COCC1.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][NH:6][S:7]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH:15]=[O:16])(=[O:9])=[O:8])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21480494N-[[3-(1,3-dioxolan-2-yl)-2-thienyl]sulfonyl]glycine ethyl ester

Product 1

HCID 21480488N-[(3-formyl-thien-2-yl)sulfonyl]glycine ethyl esterYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the product from Step A (31.0 g 97.0 mmol) in THF (100 mL) was added 3N HCl and the mixture stirred for 6 h at room temperature. Brine (100 mL) was added and the mixture extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (20.0 mL), dried (MgSO4) and evaporated to yield a white solid (22.0 g, 82%): mp 74°-76° C.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts were washed with brine (20.0 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-318a40ba4ce4467d9212f159c104f3ee
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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