Triphenylphosphine → HCID 172932298, compound

HRID 1153929Notes

Reaction equation

HRID 1153929 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:57]/[O:58][CH3:59])/[C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([O:41][CH:42]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])=[C:34]([CH2:37][I:38])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:60]1([P:66]([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C1C=CC=CC=1>[I-:38].[CH3:59][O:58]/[N:57]=[C:26](/[C:24]1[N:25]=[C:21]([NH:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:22][CH:23]=1)\[C:27]([NH:29][CH:30]1[C:55](=[O:56])[N:32]2[C:33]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:34]([CH2:37][P+:66]([C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[CH2:35][S:36][C@H:31]12)=[O:28]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13239634benzhydryl (6R)-3-(iodomethyl)-7-[[(2Z)-2-methoxyimino-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 172932298HCID 172932298, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylate (VII-1, 7.8 g, 8.4 mmoles) and triphenylphosphine (4.4 g, 16.8 mmoles) in benzene (160 ml) was stirred at room temperature for 1 hour. The resulting precipitate was collected by filtration to afford 8.0 g of the title compound VIII-1. The mother liquor was concentrated and the residue was triturated with n-hexane to yield an additional amount (1.3 g) of VIII-1. Total yield 9.3 g (93%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-6cf85231e4414360b77cb38cea8f7ec7
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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