Phosphorus pentachloride → p-Nitrobenzyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-mesyloxy-3-cephem-4-carboxylate

HRID 704265Notes

Reaction equation

HRID 704265 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.C1(CC([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[C:20]([C:29]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=4)=[O:30])=[C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:22][S:23][C@H:18]23)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C.Cl.[NH2:54][C:55]1[S:59][N:58]=[C:57]([C:60](=[N:64][O:65][CH2:66][CH3:67])[C:61](Cl)=[O:62])[N:56]=1>C(Cl)Cl.O.N1C=CC=CC=1.CO>[NH2:54][C:55]1[S:59][N:58]=[C:57]([C:60](=[N:64][O:65][CH2:66][CH3:67])[C:61]([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[C:20]([C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=4)=[O:30])=[C:21]([O:24][S:25]([CH3:28])(=[O:26])=[O:27])[CH2:22][S:23][C@H:18]23)=[O:62])[N:56]=1

Participants

9

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 867392542-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochlorideHCID 883895734-Nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate

Product 1

HCID 131716148p-Nitrobenzyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-mesyloxy-3-cephem-4-carboxylateYield 69.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of phosphorus pentachloride (57 g) in methylene chloride (1 () was added pyridine (22 ml) at -20° C. and the mixture was stirred for 30 minutes at -20° C. p-Nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate (50 g) was added to the solution at 5° C. and stirred at the same temperature for 1 hour. Methanol (56 ml) was added to the solution at -30° C. and stirred at -15° C. for 30 minutes. To the solution were added pyridine (80 ml) and diisopropylethylamine (31.4 ml) at -30° C. 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl chloride hydrochloride (syn isomer) (26.7 g) was added to the solution at -30° C. by portions and stirred at -15° C. for 1 hour Water (1 l) was added to the solution and stirred for 30 minutes. A resultant precipitate was collected by filtration and washed with diisopropyl ether and air-dried to give p-nitrobenzyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-mesyloxy-3-cephem-4-carboxylate (syn isomer) (40 g).

Workup

  1. additionwas added to the solution at 5° C.
  2. stirringstirred at -15° C. for 30 minutes
  3. additionwas added to the solution
  4. stirringstirred for 30 minutes
  5. filtrationA resultant precipitate was collected by filtration
  6. washwashed with diisopropyl ether
  7. customair-dried

Sources & evidence

ORD record
ord-be3ec432a02c489eb7560ae5186c66c3
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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