Diethyl Ether → 7beta[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate

HRID 1651153Notes

Reaction equation

HRID 1651153 reaction equation
Cl.Cl.Cl.[NH2:4][C@@H:5]1[C:23](=[O:24])[N:7]2[C:8]([C:20]([O-:22])=[O:21])=[C:9]([CH2:12][N+:13]3[N:14]([CH3:19])[C:15]([NH2:18])=[CH:16][CH:17]=3)[CH2:10][S:11][C@H:6]12.C[Si](C)(C)NC(=O)C.[NH2:33][C:34]1[S:38][N:37]=[C:36](/[C:39](=[N:47]/[O:48][CH2:49][C:50]([OH:52])=[O:51])/[C:40](OS(C)(=O)=O)=[O:41])[N:35]=1.C(OCC)C>O1CCCC1>[NH2:33][C:34]1[S:38][N:37]=[C:36]([C:39](=[N:47][O:48][CH2:49][C:50]([OH:52])=[O:51])[C:40]([NH:4][C@@H:5]2[C:23](=[O:24])[N:7]3[C:8]([C:20]([O-:22])=[O:21])=[C:9]([CH2:12][N+:13]4[N:14]([CH3:19])[C:15]([NH2:18])=[CH:16][CH:17]=4)[CH2:10][S:11][C@H:6]23)=[O:41])[N:35]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25989Acetamide, N-(trimethylsilyl)-HCID 133672892-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxyacetic acidHCID 1317163857beta-Amino-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride

Product 1

HCID 1317163867beta[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylateYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7β-amino-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride (6.96 g) and N-(trimethylsilyl)acetamide (21.8 g) in tetrahydrofuran (150 ml) was added methanesulfonyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetate (4.86 g) at ambient temperature. After being stirred for 30 minutes at the same temperature, the mixture was poured into diethyl ether (2 l), and the resultant precipitate was collected by filtration. The precipitate was dissolved in water, and the solution was adjusted to pH 2.0 with aqueous sodium bicarbonate solution. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin, Diaion HP-20. The desired product was eluted with 5% isopropyl alcohol solution and lyophilized to give 7β[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer)(5.20 g).

Workup

  1. filtrationthe resultant precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in water
  3. washThe desired product was eluted with 5% isopropyl alcohol solution

Sources & evidence

ORD record
ord-cbdc5baa72334e74a44318d26d5c7fb8
Source dataset
uspto-grants-1990_05
Patent number
US04927818

Reaction notes

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