Pyridine → HCID 53902958, compound

HRID 1077113Notes

Reaction equation

HRID 1077113 reaction equation
Cl[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].[C:47]1([P:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.N1C=CC=CC=1>C1COCC1.O1CCOCC1>[C:6]([O:5][C:3]([C: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:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:11]1=[O:46])=[P:53]([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:4])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 53963928HCID 53963928, compound

Product 1

HCID 53902958HCID 53902958, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

1-(1-chloro-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(4-tetrahydropyranyloxybut-2-ynylthio) azetidin-2-one (650mg) was dissolved in 1:1 THF/dioxan (12ml) under nitrogen. Triphenylphosphine (525mg) and pyridine (158mg) were added and the mixture heated at 55° for 15.5 hours. The reaction mixture was filtered and the filtrate evaporated. Dry toluene was added to the residue and the solution decanted from any solid and evaporated. Chromatography on silica afforded 1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4(4-tetrahydropyranyloxybut-2-ynylthio)azetidin-2-one as an amorphous solid (470mg).

Workup

  1. temperaturethe mixture heated at 55° for 15.5 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated
  4. additionDry toluene was added to the residue
  5. customthe solution decanted from any solid
  6. customevaporated

Sources & evidence

ORD record
ord-634a1a0b7d6240e5a6ff0e15cb926efc
Source dataset
uspto-grants-1976_05
Patent number
US03959267

Reaction notes

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