Pyridine → HCID 53811313, compound

HRID 1283699Notes

Reaction equation

HRID 1283699 reaction equation
Cl[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].[C:46]1([P:52]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.N1C=CC=CC=1>O1CCCC1.O1CCOCC1>[C:6]([O:5][C:3]([C: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:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=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])=[P:52]([C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:4])([CH3:7])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 53673805HCID 53673805, compound

Product 1

HCID 53811313HCID 53811313, 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-5170d4c96868407d9ce87ecd435e6e5f
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

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