Ethyl Acetate → HCID 131718129, compound

HRID 1609668Notes

Reaction equation

HRID 1609668 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:25][O:26][CH2:27][C:28]([OH:30])=[O:29])[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][Cl:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1.C(OCC)(=O)C>CN(C)C=O>[ClH:19].[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:25][O:26][CH2:27][C:28]([OH:30])=[O:29])[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][N+:32]4([CH3:31])[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH2:36][CH2:37]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 114013941-Boc-4-methylpiperazineHCID 1317189457beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid

Product 1

HCID 131718129HCID 131718129, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid (syn isomer) (4.0 g) in N,N-dimethylformamide was added dropwise 1-methyl-4-tert-butoxycarbonylpiperazine (6.7 g) at 2° C. under stirring. The stirring was continued for 1.5 hours at 18°-2° C. The reaction mixture was poured into ethyl acetate (200 ml). The resulting precipitates were collected by filtration to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(1-methyl-4-tert-butoxycarbonyl-1-piperazinio)methyl-3-cephem-4-carboxylate hydrochloride (syn isomer) (5.71 g) .

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-294c00e467b54e739a68d0c524a76f1a
Source dataset
uspto-grants-1995_03
Patent number
US05401734

Reaction notes

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