Sodium Chloride → cis-3-(2-Thienylacetamido)-2-oxoazetidine-4-carboxylic acid methyl ester

HRID 978888Notes

Reaction equation

HRID 978888 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH2:10])=[O:4].C(=O)([O-])O.[Na+].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21][C:22](Cl)=[O:23].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:22](=[O:23])[CH2:21][C:17]1[S:16][CH:20]=[CH:19][CH:18]=1)=[O:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 53988551cis-3-Amino-4-methoxycarbonyl-2-oxoazetidine

Product 1

HCID 53808761cis-3-(2-Thienylacetamido)-2-oxoazetidine-4-carboxylic acid methyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 288 mg of cis-3-amino-2-oxoazetidine-4-carboxylic acid methyl ester, 10 ml of tetrahydrofuran and 5 ml of 1N-sodium hydrogen carbonate, which is previously stirred under ice-cooling, is added dropwise a solution of 0.32 ml of 2-thienyl acetyl chloride in 10 ml of tetrahydrofuran. To the mixture, after being stirred for 10 minutes, are added 100 ml of ethyl acetate and 20 ml of a saturated aqueous solution of sodium chloride, followed by stirring, and the organic layer is separated. The aqueous layer is subjected to extraction with 30 ml of ethyl acetate, and the extract is combined with the organic layer. The whole organic layer is washed with a saturated aqueous solution of sodium chloride (20 ml×3), dried and concentrated under reduced pressure. To the residue is added 4 ml of a mixed solution (ethyl acetate:hexane=1:2), and the resulting crystals are collected by filtration and dried to afford 430 mg (80%) of cis-3-(2-thienylacetamido)-2-oxoazetidine-4-carboxylic acid methyl ester, m.p. 133°-136° C.

Workup

  1. temperaturecooling
  2. stirringTo the mixture, after being stirred for 10 minutes
  3. stirringby stirring
  4. customthe organic layer is separated
  5. extractionThe aqueous layer is subjected to extraction with 30 ml of ethyl acetate
  6. washThe whole organic layer is washed with a saturated aqueous solution of sodium chloride (20 ml×3)
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. additionTo the residue is added 4 ml of a mixed solution (ethyl acetate:hexane=1:2)
  10. filtrationthe resulting crystals are collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-dc8c4d2888474b40b520387f20c41810
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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