Phosphorus oxychloride → HCID 131715350, compound

HRID 568848Notes

Reaction equation

HRID 568848 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([CH3:16])=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:22][CH:23]1[C:40](=[O:41])[N:25]2[C:26]([C:37]([OH:39])=[O:38])=[C:27]([CH2:30][S:31][C:32]3[S:33][CH:34]=[N:35][N:36]=3)[CH2:28][S:29][C@H:24]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][C:6]([CH3:16])=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([NH:22][CH:23]2[C:40](=[O:41])[N:25]3[C:26]([C:37]([OH:39])=[O:38])=[C:27]([CH2:30][S:31][C:32]4[S:33][CH:34]=[N:35][N:36]=4)[CH2:28][S:29][C@H:24]23)=[O:12])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 53857836HCID 53857836, compound

Product 1

HCID 131715350HCID 131715350, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(2-formamido-5-methylthiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.2 g.), dimethylformamide (0.46 ml.) and phosphoryl chloride (0.54 ml.) in dry ethyl acetate (12 ml.) was added to a solution of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (2.12 g.) and trimethylsilylacetamide (6.7 g.) in dry ethyl acetate (20 ml.) at -10° to -20° C. and stirred at the same temperature for 1.5 hrs. The reaction mixture was washed with water and adjusted to pH 8 with an aqueous solution of sodium bicarbonate. The aqueous layer was separated and adjusted to pH 2 with hydrochloric acid. The precipitates were collected by filtration and dried to give 7-[2-(2-formamido-5-methylthiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 2.9 g.).

Workup

  1. washThe reaction mixture was washed with water
  2. customThe aqueous layer was separated
  3. filtrationThe precipitates were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-48c24ab0577a46ea9daa17757838601f
Source dataset
uspto-grants-1988_03
Patent number
US04729991

Reaction notes

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