Triethylamine → HCID 18600878, compound

HRID 638124Notes

Reaction equation

HRID 638124 reaction equation
[C:1]([CH:3]1[NH:6][C:5](=[O:7])[C@H:4]1[NH:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:2].C(N(CC)CC)C.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>C(Cl)Cl>[Si:35]([N:6]1[CH:3]([C:1]#[N:2])[C@H:4]([NH:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]1=[O:7])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 13232653HCID 13232653, compound

Product 1

HCID 18600878HCID 18600878, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.10 g of (3S,4RS)-4-cyano-3-tritylamino-2-azetidinone, 0.50 g of triethylamine and 20 ml of methylene chloride is added 0.56 g of tert-butyldimethylsilyl chloride under ice-cooling and stirring. The mixture is stirred at room temperature (approx. 25° C.) for 30 minutes and the reaction mixture is concentrated under reduced pressure. The residue is chromatographed on a a silicagel column [eluant: ethyl acetate-n-hexane (1:3)] to give 0.64 g of (3S,4RS)-1-tert-butyldimethylsilyl-4-cyano-3-tritylamino-2-azetidinone.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature (approx. 25° C.) for 30 minutes
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. customThe residue is chromatographed on a a silicagel column [eluant: ethyl acetate-n-hexane (1:3)]

Sources & evidence

ORD record
ord-673a42002da5469bb7d3d07f21c52594
Source dataset
uspto-grants-1985_12
Patent number
US04560508

Reaction notes

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