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

HRID 373429Notes

Reaction equation

HRID 373429 reaction equation
[ClH:1].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.Cl.[NH2:34][C:35]1[S:39][N:38]=[C:37](/[C:40](=[N:44]/[O:45][C:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])([CH3:48])[CH3:47])/[C:41]([Cl:43])=[O:42])[N:36]=1.C(OCC)C>O1CCCC1>[ClH:43].[ClH:1].[ClH:43].[NH2:34][C:35]1[S:39][N:38]=[C:37]([C:40](=[N:44][O:45][C:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])([CH3:47])[CH3:48])[C:41]([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:42])[N:36]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25989Acetamide, N-(trimethylsilyl)-HCID 87787074tert-butyl 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-chloro-2-oxoethylidene]amino]oxy-2-methylpropanoate;hydrochlorideHCID 1317163857beta-Amino-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride

Product 1

HCID 1317173227beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochlorideYield 194.8%

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 (2 g) and N-(trimethylsilyl)acetamide (6.28 g) in tetrahydrofuran (40 ml) was added (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetyl chloride hydrochloride (1.84 g) under ice-cooling. After being stirred for 1 hour, the reaction mixture was added dropwise to ethyl ether (300 ml), and the resulting precipitate was collected by filtration to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)-acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride (syn isomer) (3.4 g).

Workup

  1. temperaturecooling
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-d8bc109bcd1c4cbf9724568ad2158043
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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