Pyridine → HCID 53944058, compound

HRID 1283332Notes

Reaction equation

HRID 1283332 reaction equation
ClC([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(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1>O1CCCC1.O1CCOCC1>[C:27]1([C:26]([NH:25][CH:12]2[CH:13]([S:14][CH2:15][C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[NH:10][C:11]2=[O:45])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 53673805HCID 53673805, compound

Product 1

HCID 53944058HCID 53944058, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(1-Chloro-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) under nitrogen. Triphenylphosphine (495mg) and dry pyridine (150mg) were added and the mixture heated at 49° for 16 hours. The reaction mixture was filtered the filtrate evaporated. The residue was triturated with toluene and the soluble portion re-evaporated. Chromatography on silica afforded 1-(1-t-butoxycarbonyl)-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenylprop-2-ynylthio) azetidin-2-one, as a white solid (418mg).

Workup

  1. temperaturethe mixture heated at 49° for 16 hours
  2. filtrationThe reaction mixture was filtered the filtrate
  3. customevaporated
  4. customThe residue was triturated with toluene
  5. customthe soluble portion re-evaporated

Sources & evidence

ORD record
ord-2617cd087a874fdebe37941001461dc1
Source dataset
uspto-grants-1976_08
Patent number
US03974154

Reaction notes

Loading…