Diisopropyl Ether → HCID 178481073, compound

HRID 1031199Notes

Reaction equation

HRID 1031199 reaction equation
[NH2:1][C@@H:2]1[C:22](=[O:23])[N:4]2[C:5]([C:19]([O-:21])=[O:20])=[C:6]([CH2:9][N+:10]3[N:11]([CH3:18])[CH:12]=[C:13]([NH:15][CH:16]=[O:17])[CH:14]=3)[CH2:7][S:8][C@H:3]12.C[Si](C)(C)NC(=O)C.[NH2:32][C:33]1[S:37][N:36]=[C:35](/[C:38](=[N:46]/[O:47][CH2:48][C:49]([OH:51])=[O:50])/[C:39](OS(C)(=O)=O)=[O:40])[N:34]=1.C(OC(C)C)(C)C>O1CCCC1>[NH2:32][C:33]1[S:37][N:36]=[C:35]([C:38](=[N:46][O:47][CH2:48][C:49]([OH:51])=[O:50])[C:39]([NH:1][C@@H:2]2[C:22](=[O:23])[N:4]3[C:5]([C:19]([O-:21])=[O:20])=[C:6]([CH2:9][N+:10]4[N:11]([CH3:18])[CH:12]=[C:13]([NH:15][CH:16]=[O:17])[CH:14]=4)[CH2:7][S:8][C@H:3]23)=[O:40])[N:34]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 25989Acetamide, N-(trimethylsilyl)-HCID 133672892-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxyacetic acidHCID 178481072HCID 178481072, compound

Product 1

HCID 178481073HCID 178481073, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of di(trifluoroacetic acid) salt of 7β-amino-3-(4-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (4.0 g) and N-(trimethylsilyl)acetamide (9.29 g) in tetrahydrofuran (60 ml) was added methanesulfonyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetate (2.07 g) under ice-cooling. The mixture was stirred for 1 hour at ambient temperature and then the resulting mixture was added dropwise to diisopropyl ether. Thus produced precipitate was collected by filtration, dissolved in water and then subjected to column chromatography on macroporous non-ionic adsorption resin, Diaion HP-20 (Trademark: manufactured by Mitsubishi Chemical Industries). The desired product was eluted with 10% aqueous isopropyl alcohol solution, and then lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3- (4-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer 0.714 g).

Workup

  1. temperaturecooling
  2. filtrationThus produced precipitate was collected by filtration
  3. dissolutiondissolved in water
  4. washThe desired product was eluted with 10% aqueous isopropyl alcohol solution

Sources & evidence

ORD record
ord-03ec51221d11487685a681f7a0b1616b
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

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