HCID 21517657, compound → HCID 131710048, compound

HRID 1578886Notes

Reaction equation

HRID 1578886 reaction equation
[C:1]([O:5][C:6]([C:8]([N:28]1[CH:31]([S:32][CH2:33][C:34](=O)[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH:30]([NH:44][C:45]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:29]1=[O:64])=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[F:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][C:34]2[CH2:33][S:32][C@@H:31]3[CH:30]([NH:44][C:45]([C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[C:29](=[O:64])[N:28]3[C:8]=2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:37][CH:38]=1

Participants

3

Reactant 1

HCID 21517657HCID 21517657, compound

Product 1

HCID 131710048HCID 131710048, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenyl-2-oxopropylthio)azetidin-2-one (253 mg) was refluxed in dry dioxan (25 ml) under nitrogen for 24 hours. Evaporation of the solvent and chromatography of the residue on silica gave (IX) as a white solid (131 mg). νmax (CHCl3) 1775, 1715 cm-1 δ ppm (CDCl3) 1.52 (s, 3H), 3.01 (q, J = 17 Hz, 2H), 2.66- 3.12 (1H, exchange, D2O, 3.63 (q, J = 15Hz, 2H). 4.28 (d, J = 4.5Hz, 1H), 4.71 (multiplet collapsing to d, J = 4.5Hz on D2O exchange, 1H), 6.77-7.58 (m, aromatic).

Workup

  1. customEvaporation of the solvent and chromatography of the residue on silica

Sources & evidence

ORD record
ord-96b5fe5c7edd4aebb5d079acd3a95e82
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

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