Ammonium Chloride → HCID 10103534, compound

HRID 843727Notes

Reaction equation

HRID 843727 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Mg]Cl)C.C(O[CH:15]1[NH:18][C:17](=[O:19])[CH2:16]1)(=O)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][CH:15]1[NH:18][C:17](=[O:19])[CH2:16]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 1199814-Acetoxy-2-azetidinoneHCID 178461633HCID 178461633, compound

Product 1

HCID 10103534HCID 10103534, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of trimethylsilylacetylene (1715 ml) in tetrahydrofuran (18.0 l) was added ethyl magnesium chloride (2.0M solution in tetrahydrofuran; 6.19 l) was added dropwise below −30° C. under nitrogen atmosphere. The reaction mixture was allowed to 0° C. and stirred for 1 hour. After cooling to −30° C., 4-acetoxy-2-azetidinone (320 g) was added and warmed to room temperature, and stirred for 2 hours. After cooling to −20° C., saturated ammonium chloride (4.0 l) was added. Ethyl acetate (20 l) was added and washed with water (10 l×2) and brine. The organic layer was dried over magnesium sulfate, filtered off and evaporated in vacuo to give 4-(2-trimethylsilylethynyl)-2-azetidinone (425 g), which was essentially pure, so it was used to the next step without further purification.

Workup

  1. additionwas added dropwise below −30° C. under nitrogen atmosphere
  2. customwas allowed to 0° C.
  3. temperaturewarmed to room temperature
  4. stirringstirred for 2 hours
  5. temperatureAfter cooling to −20° C.
  6. washwashed with water (10 l×2) and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered off
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a6aff19604ca4e389119dc6f42241f3c
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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