Pyridine → HCID 53673805, compound

HRID 1077107Notes

Reaction equation

HRID 1077107 reaction equation
O[CH:2]([N:10]1[CH:13]([S:14][CH2:15][C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:12]([NH:25][C:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:11]1=[O:45])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].N1C=CC=CC=1.S(Cl)([Cl:54])=O>O1CCCC1.O1CCOCC1>[Cl:54][CH:2]([N:10]1[CH:13]([S:14][CH2:15][C:16]#[C:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:12]([NH:25][C:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:11]1=[O:45])[C:3]([O:5][C:6]([CH3:8])([CH3:7])[CH3:9])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 53736911HCID 53736911, compound

Product 1

HCID 53673805HCID 53673805, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent3×

Procedure

1(1-Hydroxy-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenylprop-2-ynylthio)azetidin-2-one (570mg) was dissolved in a 1:1 mixture of dry tetrahydrofuran and dioxan (20ml) and the solution, under nitrogen, was cooled to -10°. Pyridine (224mg) in dry dioxan (5ml) was then added, followed by the dropwise addition of thionyl chloride (0.206ml) in dry dioxan (5ml) over 2-3 minutes. After a further 15 minutes the precipitated solid was filtered off and the filtrate evaporated to dryness. Dry toluene was added and was decanted from any solid. The organic solution was evaporated to dryness and re-evaporation from dry ether gave 1-(1-Chloro-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenylprop-2-ynylthio)azetidin-2-one as an amorphous solid.

Workup

  1. temperaturethe solution, under nitrogen, was cooled to -10°
  2. filtrationAfter a further 15 minutes the precipitated solid was filtered off
  3. customthe filtrate evaporated to dryness
  4. additionDry toluene was added
  5. customwas decanted from any solid
  6. customThe organic solution was evaporated to dryness and re-evaporation from dry ether

Sources & evidence

ORD record
ord-d3110ad8bff54ff2a28a717e74d5c3f6
Source dataset
uspto-grants-1976_05
Patent number
US03959267

Reaction notes

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