Phosphorus oxychloride → HCID 131712951, compound

HRID 1758068Notes

Reaction equation

HRID 1758068 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[C:11]([C:12](=[N:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([OH:15])=O)=[CH:10][S:9][CH2:8][CH2:7]1.[NH2:24][CH:25]1[C:42](=[O:43])[N:27]2[C:28]([C:39]([OH:41])=[O:40])=[C:29]([CH2:32][S:33][C:34]3[S:35][CH:36]=[N:37][N:38]=3)[CH2:30][S:31][C@H:26]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[O:6]1[C:11]([C:12](=[N:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([NH:24][CH:25]2[C:42](=[O:43])[N:27]3[C:28]([C:39]([OH:41])=[O:40])=[C:29]([CH2:32][S:33][C:34]4[S:35][CH:36]=[N:37][N:38]=4)[CH2:30][S:31][C@H:26]23)=[O:15])=[CH:10][S:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 54300440HCID 54300440, compound

Product 1

HCID 131712951HCID 131712951, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

Phosphoryl chloride (1.214 g.), N,N-dimethylformamide (0.579 g.) and ethyl acetate (3 ml.) were treated in a conventional manner to give a Vilmeier reagent. To the solution were added ethyl acetate (7 ml.) and 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 2.18 g.) and treated in a similar manner to that of Example 24 to give an activated acid solution. The solution was added to a solution of 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (2.18 g.) and trimethylsilylacetamide (6.93 g.) in ethyl acetate (50 ml.), and the mixture was treated in a similar manner to that of Example 24 to give 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-hexyloxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 3.00 g.)

Workup

  1. customto give a Vilmeier reagent
  2. additiontreated in a similar manner to that of Example 24
  3. customto give an activated acid solution
  4. additionthe mixture was treated in a similar manner to that of Example 24

Sources & evidence

ORD record
ord-11a8cf029f9349bf9cc4e4397c993236
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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