2,5-Dimethoxytetrahydrofuran → 2-Sulfo-2-(1-pyrryl)acetic acid

HRID 26316Notes

Reaction equation

HRID 26316 reaction equation
C([O-])(=O)C.[Na+].Cl.[S:7]([CH:11]([NH2:15])[C:12]([OH:14])=[O:13])([OH:10])(=[O:9])=[O:8].CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>C(O)(=O)C.C(OC(=O)C)C>[S:7]([CH:11]([N:15]1[CH:18]=[CH:22][CH:21]=[CH:20]1)[C:12]([OH:14])=[O:13])([OH:10])(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 86736466alpha-Sulfo-alpha-aminoacetic acid hydrochloride

Product 1

HCID 867364652-Sulfo-2-(1-pyrryl)acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium acetate (0.1 mole) in about 300 ml of glacial acetic acid is added about 0.05 mole of α-sulfo-α-aminoacetic acid hydrochloride. The solution is heated to reflux for 5 minutes, 2,5-dimethoxytetrahydrofuran (1 equivalent based on α-sulfo-α-aminoacetic acid hydrochloride) is added as quickly as possible, and the solution refluxed for an additional 2 minutes. The acetic acid is flash evaporated leaving a residue which is taken up in ethylacetate. The ethyl acetate is filtered, dried and evaporated to give α-sulfo-α-(1-pyrryl) acetic acid.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 5 minutes
  3. temperaturerefluxed for an additional 2 minutes
  4. customevaporated
  5. customleaving a residue which
  6. filtrationThe ethyl acetate is filtered
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-6e1284b316994e4b8f3c00440d36aaba
Source dataset
uspto-grants-1979_04
Patent number
US04148998

Reaction notes

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