Dicyclohexylcarbodiimide → HCID 53748691, compound

HRID 2285796Notes

Reaction equation

HRID 2285796 reaction equation
[CH2:1]1[S:16][CH:5]([CH2:6][C@@H:7]([NH2:15])[C@H](C(O)=O)[C@@H](C)O)[S:4][CH2:3][CH2:2]1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH2:1]1[S:16][C:5]2([CH2:6][CH2:7][NH:15]2)[S:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 12803412HCID 12803412, compound

Product 1

HCID 53748691HCID 53748691, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-amino-4-C-carboxy-2,3,4,6-tetradeoxy-D-arabino-hexose trimethylene dithioacetal (810 mg, 3.05 mmol) in acetonitrile (15 ml) is treated with N,N'-dicyclohexylcarbodiimide (689 mg, 3.34 mmol). The resulting mixture is kept at room temperature for 10 minutes and then heated at 60° for 5 hours. The reaction mixture is concentrated, the residue is slurried in ethyl acetate, and the precipitated urea is removed by filtration. The filtrate is washed successively with N aqueous hydrochloric acid, saturated aqueous sodium hydrogen-carbonate, water, dried (magnesium sulfate), and evaporated under vacuum to yield 385 mg (51%) of the desired 2-azetidinone trimethylene dithioacetal.

Workup

  1. temperatureheated at 60° for 5 hours
  2. concentrationThe reaction mixture is concentrated
  3. customthe precipitated urea is removed by filtration
  4. washThe filtrate is washed successively with N aqueous hydrochloric acid, saturated aqueous sodium hydrogen-carbonate, water
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-df2952868fdb4373a843c69a43c0464b
Source dataset
uspto-grants-1982_04
Patent number
US04324900

Reaction notes

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