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Ethyl Acetate → Benzhydryl 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

HRID 1734268
Notes
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Reaction equation

HRID 1734268 reaction equation
Cl.[NH2:2][C@@H:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12.C[Si](C)(C)NC(=O)C.CS([O:42][C:43](=O)[C:44]([C:51]1[N:55]=[C:54]([NH2:56])[S:53][N:52]=1)=[N:45][O:46][CH2:47][C:48]([OH:50])=[O:49])(=O)=O.C(OCC)(=O)C>O1CCCC1.O>[NH2:56][C:54]1[S:53][N:52]=[C:51]([C:44](=[N:45][O:46][CH2:47][C:48]([OH:50])=[O:49])[C:43]([NH:2][C@@H:3]2[C:28](=[O:29])[N:5]3[C:6]([C:12]([O:14][CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]23)=[O:42])[N:55]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25989Acetamide, N-(trimethylsilyl)-HCID 132396287-Amino-3-chloromethyl-3-cephem-4-carboxylic acid diphenylmethyl ester hydrochlorideHCID 536554152-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetic methanesulfonic anhydride

Product 1

HCID 131718944
Benzhydryl 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate
Yield 53.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7β-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (22.6 g) and N-trimethylsilylacetamide (25.0 g) in tetrahydrofuran (250 ml) was added 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetic methanesulfonic anhydride (syn isomer) (19.8 g) at 0°-5° C. under stirring. The stirring was continued for an hour at the same temperature. The reaction mixture was poured into a mixture of ethyl acetate (500 ml) and water (500 ml). The organic layer was separated, washed with water twice and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then concentrated in vacuo. To the residue was added diethyl ether and then the resulting precipitates were collected by filtration to give benzhydryl 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (17.2 g).

Workup

  1. waitThe stirring was continued for an hour at the same temperature
  2. customThe organic layer was separated
  3. washwashed with water twice
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionTo the residue was added diethyl ether
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-683643eb3ad74664a2d6949db84d5269
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05532354

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes