Triphenylphosphine → [(6R)-2-benzhydryloxycarbonyl-7-[[(2Z)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclobutyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl-triphenylphosphanium iodide

HRID 1153931Notes

Reaction equation

HRID 1153931 reaction equation
[C:1]([O:5][C:6]([C:8]1([O:12]/[N:13]=[C:14](/[C:45]2[N:46]=[C:47]([NH:50][C:51]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[S:48][CH:49]=2)\[C:15]([NH:17][CH:18]2[C:43](=[O:44])[N:20]3[C:21]([C:27]([O:29][CH:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])=[C:22]([CH2:25][I:26])[CH2:23][S:24][C@H:19]23)=[O:16])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:70]1([P:76]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>C1C=CC=CC=1.CCCCCC>[I-:26].[C:1]([O:5][C:6]([C:8]1([O:12]/[N:13]=[C:14](/[C:45]2[N:46]=[C:47]([NH:50][C:51]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[S:48][CH:49]=2)\[C:15]([NH:17][CH:18]2[C:43](=[O:44])[N:20]3[C:21]([C:27]([O:29][CH:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])=[C:22]([CH2:25][P+:76]([C:77]4[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=4)([C:83]4[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=4)[C:70]4[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 172953015benzhydryl (6R)-3-(iodomethyl)-7-[[(2Z)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclobutyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 172941329[(6R)-2-benzhydryloxycarbonyl-7-[[(2Z)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclobutyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl-triphenylphosphanium iodideYield 94%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(1-t-butoxycarbonylcyclobut-1-oxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate (VII-5', 6.4 g, 6 mmoles) and triphenylphosphine (2.4 g, 9 mmoles) in benzene (120 ml) was stirred at room temperature for 2 hours and diluted with n-hexane (ca. 500 ml). The resulting precipitate was collected by filtration to afford 7.5 g (94%) of the title compound VIII-B 5'.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0d2ecb2137074a178e0977ef9b223754
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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