Pyridine → HCID 21517629, compound

HRID 1283701Notes

Reaction equation

HRID 1283701 reaction equation
O[CH:2]([N:10]1[CH:13]([S:14][CH2:15][C:16]#[C:17][CH3:18])[CH:12]([NH:19][C:20]([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:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:39])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].N1C=CC=CC=1.S(Cl)([Cl:48])=O>O1CCCC1.O1CCOCC1>[Cl:48][CH:2]([N:10]1[CH:13]([S:14][CH2:15][C:16]#[C:17][CH3:18])[CH:12]([NH:19][C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:11]1=[O:39])[C:3]([O:5][C:6]([CH3:8])([CH3:7])[CH3:9])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 21517661HCID 21517661, compound

Product 1

HCID 21517629HCID 21517629, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent3×

Procedure

1-(1-Hydroxy-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(but-2-ynylthio)azetidin-2-one (0.44g) was dissolved in a 1:1 mixture of dry tetrahydrofuran and dioxan (10ml) and the solution, under nitrogen, was cooled to -10°. Pyridine (0.2g) in dry dioxan (2.5ml) was added, followed by the dropwise addition of thionyl chloride (0.19ml) in dioxan (2.5ml) 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 to the residue and decanted off 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-(but-2-ynylthio)azetidin-2-one as an amorphous solid (0.45g).

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 to the residue
  5. customdecanted off from any solid
  6. customThe organic solution was evaporated to dryness and re-evaporation from dry ether

Sources & evidence

ORD record
ord-5270ef2f53304544ad2fd07085ac90b3
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

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