Sodium Iodide → benzhydryl (6R)-3-(iodomethyl)-8-oxo-7-[[(2Z)-2-prop-2-ynoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 615787Notes

Reaction equation

HRID 615787 reaction equation
Cl[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:26]([NH:27][C:28](=[O:60])/[C:29](=[N:55]\[O:56][CH2:57][C:58]#[CH:59])/[C:30]3[N:31]=[C:32]([NH:35][C:36]([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)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[S:33][CH:34]=3)[C:25](=[O:61])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[Na+].[I-:63]>CC(C)=O>[CH2:57]([O:56]/[N:55]=[C:29](/[C:30]1[N:31]=[C:32]([NH:35][C:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:33][CH:34]=1)\[C:28]([NH:27][CH:26]1[C:25](=[O:61])[N:7]2[C:8]([C:9]([O:11][CH:12]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])=[C:3]([CH2:2][I:63])[CH2:4][S:5][C@H:6]12)=[O:60])[C:58]#[CH:59]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 88600476benzhydryl (6R)-3-(chloromethyl)-8-oxo-7-[[(2Z)-2-prop-2-ynoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 88600779benzhydryl (6R)-3-(iodomethyl)-8-oxo-7-[[(2Z)-2-prop-2-ynoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 100.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of diphenylmethyl 3-chloromethyl-7-[(Z)-2-propargyloxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (VI-f) (2.0 g, 2.3 mmoles) and NaI (1.04 g, 6.9 mmoles) in acetone (40 ml) was stirred for 1 hour. The mixture was filtered and the filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous Na2S2O3, water and a saturated aqueous NaCl, successively. It was then dried over MgSO4 and evaporated to give 2.2 g (98%) of the title compound [VII-f].

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 5% aqueous Na2S2O3, water
  5. dry with materialIt was then dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-c5edf76d97224691903d530ba90969a4
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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