Triphenylphosphine → HCID 56623486, compound

HRID 1710255Notes

Reaction equation

HRID 1710255 reaction equation
S(Cl)(Cl)=O.[N+](C1C=CC(COC(=O)CO)=CC=1)([O-])=O.[C:20]1([P:26]([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)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[N+:39]([C:42]1[CH:80]=[CH:79][C:45]([CH2:46][O:47][C:48](=[O:78])[CH:49]([N:51]2[C@H:54]([S:55][C:56](=[O:74])[CH2:57][CH2:58][CH2:59][NH:60][C:61]([O:63][CH2:64][C:65]3[CH:70]=[CH:69][C:68]([N+:71]([O-:73])=[O:72])=[CH:67][CH:66]=3)=[O:62])[C@@H:53]([O:75][CH3:76])[C:52]2=[O:77])Cl)=[CH:44][CH:43]=1)([O-:41])=[O:40]>O1CCCC1.C(Cl)Cl.C(N(CC)CC)C>[N+:39]([C:42]1[CH:43]=[CH:44][C:45]([CH2:46][O:47][C:48](=[O:78])[C:49]([N:51]2[C@H:54]([S:55][C:56](=[O:74])[CH2:57][CH2:58][CH2:59][NH:60][C:61]([O:63][CH2:64][C:65]3[CH:70]=[CH:69][C:68]([N+:71]([O-:73])=[O:72])=[CH:67][CH:66]=3)=[O:62])[C@@H:53]([O:75][CH3:76])[C:52]2=[O:77])=[P:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:79][CH:80]=1)([O-:41])=[O:40]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 14136080HCID 14136080, compoundHCID 56626509HCID 56626509, compound

Product 1

HCID 56623486HCID 56623486, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

Analogously to Example 24, 0.12 ml of thionyl chloride and then 0.23 ml of triethylamine in 0.23 ml of absolute tetrahydrofuran are added to a solution of 606 mg of 2-[(3S,4R)-4-p-nitrobenzyloxycarbonylaminobutyrylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester in 4.5 ml of absolute tetrahydrofuran. After reacting and working up, 0.54 g of triphenylphosphine is added to the resulting crude 2-[(3S,4R)-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester in 1.15 ml of absolute tetrahydrofuran. Working up and chromatography over silica gel produce the title compound with the following IR spectrum (CH2Cl2): characteristic absorption bands at 5.7, 5.78, 5.9, 6.15, 6.55, 7.45 and 8.26μ.

Sources & evidence

ORD record
ord-3f9f90eabf6d4bcf8a9070f905f69e03
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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