Iodine → HCID 136485905, compound

HRID 247158Notes

Reaction equation

HRID 247158 reaction equation
O[CH2:2][C:3]1[CH2:10][S:9][C@H:8]2[N:5]([C:6](=[O:20])[C@H:7]2[N:11]=[CH:12][C:13]2[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=2)[OH:15])[C:4]=1[C:21]([O:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].[C:37]1([P:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[I:56]I.C(O)(C)C>CN(C)C=O.O1CCCC1>[I-:56].[CH:24]([O:23][C:21]([C:4]1[N:5]2[C@H:8]([S:9][CH2:10][C:3]=1[CH2:2][P+:43]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C@H:7]([N:11]=[CH:12][C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15])[C:6]2=[O:20])=[O:22])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 807IodineHCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 136132858HCID 136132858, compound

Product 1

HCID 136485905HCID 136485905, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl (6R,7R)-3-hydroxymethyl-8-oxo-7-salicylideneamino-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (33 g) and triphenylphosphine (37.2 g) in N,N-dimethylformamide (90 ml) was added dropwise a solution of iodine (19.5 g) in tetrahydrofuran (30 ml) at 15° C., and the mixture was stirred for 15 minutes. The reaction mixture was poured into isopropyl alcohol (1200 ml) and then stirred for 2 hours. The precipitated crystals were collected by filtration to give (6R,7R)-2-benzhydryloxycarbonyl-8-oxo-7-salicylideneamino-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3-ylmethyl-triphenyl-phosphonium iodide almost quantitatively.

Workup

  1. stirringstirred for 2 hours
  2. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7545fa118cb54337aeea091549f9062d
Source dataset
uspto-grants-1987_11
Patent number
US04705851

Reaction notes

Loading…