Phosphorus oxychloride → HCID 131712950, compound

HRID 1758067Notes

Reaction equation

HRID 1758067 reaction equation
P(Cl)(Cl)(Cl)=O.C[N+](C)=CCl.[Cl-].[O:12]1[C:17]([C:18](=[N:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:19]([OH:21])=O)=[CH:16][S:15][CH2:14][CH2:13]1.C[Si](CC(N)=O)(C)C.[NH2:38][CH:39]1[C:57](=[O:58])[N:41]2[C:42]([C:54]([OH:56])=[O:55])=[C:43]([CH2:46][S:47][C:48]3[N:52]([CH3:53])[N:51]=[N:50][N:49]=3)[CH2:44][S:45][C@H:40]12>C(OCC)(=O)C.O.CN(C)C=O>[O:12]1[C:17]([C:18](=[N:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:19]([NH:38][CH:39]2[C:57](=[O:58])[N:41]3[C:42]([C:54]([OH:56])=[O:55])=[C:43]([CH2:46][S:47][C:48]4[N:52]([CH3:53])[N:51]=[N:50][N:49]=4)[CH2:44][S:45][C@H:40]23)=[O:21])=[CH:16][S:15][CH2:14][CH2:13]1

Participants

9

Reactant 5

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 54300440HCID 54300440, compound

Product 1

HCID 131712950HCID 131712950, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Phosphoryl chloride (1.214 g.), N,N-dimethylformamide (0.579 g.) and ethyl acetate (3 ml.) were treated in a conventional manner to prepare a Vilsmeier reagent. To the reagent was added 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 2.00 g.) at -10° C., and stirred at the same temperature for 20 minutes. On the other hand, trimethylsilylacetamide (6.93 g.) was added to a suspension of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.18 g.) in ethyl acetate (50 ml.), and stirred at 40° C. for an hour. To the solution was added the activated acid solution at -10° C. and stirred at the same temperature for an hour. Water (20 ml.) was added to the resultant solution and the organic layer was separated. The solution was washed with water (20 ml.) twice and dried. After concentrating the solution in vacuo, the residue was pulverized with diisopropyl ether (50 ml.). The precipitates were collected by filtration and dried to give 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-hexyloxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 3.4 g.).

Workup

  1. stirringstirred at 40° C. for an hour
  2. additionTo the solution was added the activated acid solution at -10° C.
  3. stirringstirred at the same temperature for an hour
  4. customthe organic layer was separated
  5. washThe solution was washed with water (20 ml.) twice
  6. customdried
  7. concentrationAfter concentrating the solution in vacuo
  8. filtrationThe precipitates were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-eb9b94b76e4c4d5388f29c45d2421839
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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