Pyridine → HCID 53963928, compound

HRID 1283336Notes

Reaction equation

HRID 1283336 reaction equation
O[CH:2]([N:10]1[CH:13]([S:14][CH2:15][C:16]#[C:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:12]([NH:26][C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:11]1=[O:46])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].N1C=CC=CC=1.S(Cl)([Cl:55])=O>C1COCC1.O1CCOCC1.O1CCOCC1>[Cl:55][CH:2]([N:10]1[CH:13]([S:14][CH2:15][C:16]#[C:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:12]([NH:26][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:11]1=[O:46])[C:3]([O:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 21517608HCID 21517608, compound

Product 1

HCID 53963928HCID 53963928, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22018518Dioxane tetrahydrofuranSolvent2×

Procedure

1-(1-Hydroxy-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(4-tetrahydropyranyloxybut-2-ynylthio) azetidin-2-one (646mg) was dissolved in dry THF/dioxan (1:1, 12ml) and the solution, under nitrogen, was cooled to -15°. Dry pyridine (227mg) in dioxan (1ml) was then added followed by the dropwise addition of thionyl chloride (357mg) in 1:1 tetrahydrofuran/dioxan (5ml) over 1-2 minutes. After a further 15 minutes the precipitated solid was filtered off and the filtrate evaporated to dryness. Dry toluene was added and the solution decanted from any solid, and evaporated to give 1-(1-chloro-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(4-tetrahydropyranyloxybut-2-ynylthio)azetidine-2-one as an amorphous solid (650mg) after drying overnight in vacuo.

Workup

  1. temperaturethe solution, under nitrogen, was cooled to -15°
  2. filtrationAfter a further 15 minutes the precipitated solid was filtered off
  3. customthe filtrate evaporated to dryness
  4. additionDry toluene was added
  5. customthe solution decanted from any solid
  6. customevaporated

Sources & evidence

ORD record
ord-bd376f33ccd546bb85d4a49ee434e3c1
Source dataset
uspto-grants-1976_08
Patent number
US03974154

Reaction notes

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