Potassium Fluoride → HCID 15058003, compound

HRID 1906597Notes

Reaction equation

HRID 1906597 reaction equation
[C:1]([NH:20][C@H:21]1[C@H:24]([C:25]#[C:26][Si](C)(C)C)[NH:23][C:22]1=[O:31])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[K+]>C(O)C.CS(C)=O.CCOCC>[C:25]([C@@H:24]1[NH:23][C:22](=[O:31])[C@H:21]1[NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[CH:26]

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 15058001HCID 15058001, compound

Product 1

HCID 15058003HCID 15058003, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

10.0 g (0.024 mol) of (3S,4S)-3-tritylamino-4-[2-(trimethylsilyl)ethynyl]-2-azetidinone and 1.5 g (0.026 mol) of potassium fluoride are stirred at 20° C. for 1.5 hours in 100 ml of ethanol and 100 ml of dimethyl sulphoxide. The solution is diluted with ether, the ether phase is washed with water, dried and evaporated. 8.1 g (85%) of crude (3S,4S)-4-ethynyl-3-tritylamino-2-azetidinone are obtained.

Workup

  1. washthe ether phase is washed with water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-aec3ba8b0e52417dadc3ba68bc4dda67
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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