Acetyl chloride → HCID 86741566, compound

HRID 652211Notes

Reaction equation

HRID 652211 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]2[CH2:15][NH:14][C:13]2=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19].C[Si](C)(C)[N:26]([CH3:31])[Si](C)(C)C.[C:34](Cl)(=[O:36])[CH3:35]>O1CCCC1>[C:34]([CH2:31][NH:26][S:18]([NH:21][C:22]([N:14]1[CH2:15][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:13]1=[O:16])=[O:23])(=[O:20])=[O:19])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 70199Silanamine, N,1,1,1-tetramethyl-N-(trimethylsilyl)-HCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Product 1

HCID 86741566HCID 86741566, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2-azetidinone (2.2 g) was suspended in 100 ml of anhydrous tetrahydrofuran and cooled to -50° C. with stirring. Chlorosulfonylisocyanate (1.56 g) was added and the temperature was maintained at 0° C. for 30 minutes. After this time 3.51 g of heptamethyl disilazane was added and stirring at room temperature was continued overnight. Acetyl chloride (3.14 g) was added and the solution was stirred for an additional 48 hours. The solvent was removed in vacuo, and the residue dissolved in ethyl acetate and extracted twice with 50 ml portions of water. The aqueous layer was discarded and the ethyl acetate solution was dried with Na2SO4 and evaporated to dryness. The residue was dissolved in acetone/water (9:1), the pH adjusted to 6.5 with 1N KOH and the acetone removed in vacuo. The remaining aqueous solution was freeze-dried. The resulting crude compound (1.9 g) was purified by HP-20 chromatography, yielding 1.03 g of product.

Workup

  1. temperaturethe temperature was maintained at 0° C. for 30 minutes
  2. stirringstirring at room temperature
  3. stirringthe solution was stirred for an additional 48 hours
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate
  6. extractionextracted twice with 50 ml portions of water
  7. dry with materialthe ethyl acetate solution was dried with Na2SO4
  8. customevaporated to dryness
  9. dissolutionThe residue was dissolved in acetone/water (9:1)
  10. customthe acetone removed in vacuo
  11. customThe remaining aqueous solution was freeze-dried
  12. customThe resulting crude compound (1.9 g) was purified by HP-20 chromatography

Sources & evidence

ORD record
ord-76f762af01fa4de2a65370f90207bc65
Source dataset
uspto-grants-1987_06
Patent number
US04670553

Reaction notes

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