HCID 21517660, compound → HCID 68137441, compound

HRID 1578883Notes

Reaction equation

HRID 1578883 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][CH:39]=[CH:38][CH:37]=2)[CH:30]([NH:43][C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:29]1=[O:63])=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[CH2:35]([C:34]1[CH2:33][S:32][C@@H:31]2[CH:30]([NH:43][C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:29](=[O:63])[N:28]2[C:8]=1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 1

HCID 21517660HCID 21517660, compound

Product 1

HCID 68137441HCID 68137441, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(1-t-Butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-phenyl-2-oxopropylthio)azetidin- 2-one (331 mg) was refluxed in dry dioxan (15 ml) under nitrogen for 25 hours. Evaporation of the solvent and chromatography of the residue on silica gave (III) (141 mg). νmax (CHCl3) 3480, 1775, 1710, 1630 cm-1 δ ppm (CDCl3) 1.5 (s.9H), 2.95 (d.1H. J= 10Hz, D2O exchange), 3.00 (centre of AB quartet), 3.68 (centre of AB quartet, J= 15Hz), 4.25 (d. 1H. J= 5Hz), 4.70 (q. 1H, J= 5Hz, 10Hz, collapsing to a doublet, J= 5Hz, on D2O exchange), 7.1-7.7 (m, 20H).

Workup

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

Sources & evidence

ORD record
ord-29bfefe8ae484e2dba774730cf38eac9
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

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