Chlorosulfonyl isocyanate → HCID 86741565, compound

HRID 652210Notes

Reaction equation

HRID 652210 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)[NH:26][C:27](=[O:30])[CH2:28][Cl:29]>C(OCC)(=O)C>[Cl:29][CH2:28][C:27]([NH:26][S:18]([NH:21][C:22]([N:14]1[CH2:15][CH: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:30]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 201995622-Chloro-N-(trimethylsilyl)acetamide

Product 1

HCID 86741565HCID 86741565, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-50 °C

Procedure

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2-azetidinone (4.4 g) was suspended in 150 ml of dry ethyl acetate. The mixture was cooled to -50° C. and 3.3 g of chlorosulfonyl isocyanate was added with stirring; stirring was continued without cooling until the temperature reached 0° C. N-(Trimethylsilyl)chloroacetamide (6.0 g) was added and the solution was stirred overnight. The insoluble material was filtered off and the filtrate washed with water. The organic layer was extracted twice with saturated aqueous sodium bicarbonate. The alkaline aqueous layer was acidified to pH 1 with 20% hydrochloric acid and extracted twice with 150 ml portions of ethyl acetate. The organic layers were combined, dried and evaporated to dryness. The oily residue was dissolved in 50 ml of acetone and the pH was adjusted to 6.5 by addition of lN potassium hydroxide. The solvent was removed in vacuo and the crystalline residue filtered with ether, yielding 3.9 g of the title compound.

Workup

  1. stirringstirring
  2. temperaturewithout cooling until the temperature
  3. customreached 0° C
  4. stirringthe solution was stirred overnight
  5. filtrationThe insoluble material was filtered off
  6. washthe filtrate washed with water
  7. extractionThe organic layer was extracted twice with saturated aqueous sodium bicarbonate
  8. extractionextracted twice with 150 ml portions of ethyl acetate
  9. customdried
  10. customevaporated to dryness
  11. dissolutionThe oily residue was dissolved in 50 ml of acetone
  12. additionthe pH was adjusted to 6.5 by addition of lN potassium hydroxide
  13. customThe solvent was removed in vacuo
  14. filtrationthe crystalline residue filtered with ether

Sources & evidence

ORD record
ord-2fbf6620fea6428f897572755ea891bb
Source dataset
uspto-grants-1987_06
Patent number
US04670553

Reaction notes

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