(Diethylamino)sulfur trifluoride → HCID 13471581, compound

HRID 2413883Notes

Reaction equation

HRID 2413883 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:17][C:18](=[O:28])[CH2:19][CH:20]1[NH:23][C:22](=[O:24])[CH:21]1[CH:25](O)[CH3:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>ClCCl>[CH2:10]([O:17][C:18](=[O:28])[CH2:19][CH:20]1[NH:23][C:22](=[O:24])[CH:21]1[CH:25]([F:7])[CH3:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 13018169HCID 13018169, compound

Product 1

HCID 13471581HCID 13471581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a -78° cooled solution of 1.5 ml of diethylaminosulphurtrifluoride in 4 ml of dry dichloromethane is added a solution of 2.52 g of (3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester (prepared analogously to D. G. Melillo et.al., Tetrahedron Letters 21, 2783 [1980]) in 4 ml of abs. dichloromethane. The mixture is stirred for 5 minutes at -78° and mixed with excess cold saturated NaHCO3. After addition of further dichloromethane the phases are separated, the organic phase dried over magnesium sulphate and evaporated to dryness. Chromatography of the residue over silica gel (cyclohexane/ethylacetate=2/1) yields the title compound m.p. 40°-43°.

Workup

  1. customprepared analogously to D
  2. customare separated
  3. dry with materialthe organic phase dried over magnesium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7efcfe0121464c61bfd0840c4126c8d7
Source dataset
uspto-grants-1988_01
Patent number
US04720491

Reaction notes

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