Ammonium Chloride → HCID 18734916, compound

HRID 843731Notes

Reaction equation

HRID 843731 reaction equation
[Si:1]([N:8]1[C@H:11]([CH:12]=[C:13](Br)Br)[CH2:10][C:9]1=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[NH4+].[Cl-]>>[Si:1]([N:8]1[C@H:11]([C:12]#[CH:13])[CH2:10][C:9]1=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 11057705HCID 11057705, compound

Product 1

HCID 18734916HCID 18734916, compoundYield 56%

Conditions

Temperature
-75 °C

Procedure

To a solution of (s)-N-tert-butyldimethylsilyl-4 (2,2-dibromoethenyl)-2-azetidinone (0.63 g) was added lithium bis(trimethylsilyl)amide (3.75 ml, 1 mol solution in n-hexane) at −75° C. After stirring at −75° C. for 1 hour, a saturated aqueous NH4Cl solution was added and extracted with ethyl acetate. The extract was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with (diethyl ether:n-hexane=1:5) to give (S)-N-tert-butyldimethylsilyl-4-ethynyl-2-azetidinone (0.20 g) as an colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel eluting with (diethyl ether:n-hexane=1:5)

Sources & evidence

ORD record
ord-d0b05d1c05684ac5954b7825ed3e514e
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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