Sodium Iodide → HCID 88625133, compound

HRID 464217Notes

Reaction equation

HRID 464217 reaction equation
[I-:1].[Na+].[NH2:3][CH:4]1[C:29](=[O:30])[N:6]2[C:7]([C:13]([O:15][CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[C:8]([CH2:11][Cl:12])[CH2:9][S:10][C@H:5]12.[C:31]1([P:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C)C=O>[ClH:12].[I-:1].[CH:16]([O:15][C:13]([C:7]1[N:6]2[C:29](=[O:30])[CH:4]([NH2:3])[C@H:5]2[S:10][CH2:9][C:8]=1[CH2:11][P+:37]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:14])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 88625133HCID 88625133, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium iodide (1.8 g) was added to a solution of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate (5.0 g) and triphenylphosphine (3.2 g) in dimethyl formamide (15 ml) under ice-cooling and stirred for 3 hours at ambient temperature. The resulting solution was added dropwise to ethyl acetate (250 ml) under vigorous stirring. The precipitate, collected by filtration, was washed with ethyl acetate to give [4-benzhydryloxycarbonyl-7-amino-3-cephem-3-ylmethyl]triphenylphosphonium iodide hydrochloride (9.6 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitate, collected by filtration
  3. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-2f5ca0ad8cbc4170ae62fcbc9e4ac98f
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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