Ammonia → 7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

HRID 543537

Reaction equation

HRID 543537 reaction equation
[Na].[SH:2][C:3]1[N:7]([CH3:8])[N:6]=[N:5][N:4]=1.CC(O[CH2:13][C:14]1[CH2:23][S:22][C@@H:17]2[C@H:18]([NH2:21])[C:19](=[O:20])[N:16]2[C:15]=1[C:24]([OH:26])=[O:25])=O.P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.COC(C1C(Cl)=C(Cl)C(C(OC)=O)=C(Cl)C=1Cl)=O.N>C(#N)C>[NH2:21][CH:18]1[C:19](=[O:20])[N:16]2[C:15]([C:24]([OH:26])=[O:25])=[C:14]([CH2:13][S:2][C:3]3[N:7]([CH3:8])[N:6]=[N:5][N:4]=3)[CH2:23][S:22][C@H:17]12

Participants

7

Reactant 5

HCID 222AmmoniaHCID 2943DacthalHCID 4413287-Aminocephalosporanic acidHCID 4432411Diphosphoryl tetrachlorideHCID 178482029HCID 178482029, compound

Product 1

HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A 3.5 ml portion of acetonitrile was added to 0.570 g of dihydrate of 5-mercapto-1-methyl-1H-tetrazole sodium salt and 0.680 g of 7-ACA, and 1.64 g of diphosphoryl tetrachloride was added dropwise to the mixture under cooling over an external bath at -30° to -20° C., followed by adding 2.29 g of DCPA and rinsing with 0.5 ml of acetonitrile. The reaction solution was stirred at -5° to 0° C. for 5 minutes, warmed at 25° C., and stirred for 40 minutes to allow the reaction to proceed. The reaction solution was cooled and poured into ice-water, which was placed in a refrigerator overnight. The mixture was adjusted to pH 4.0 with 25% aqueous ammonia, and the resultant precipitate was recovered by filtration, washed with cold water and acetone successively and dried, thereby affording 0.732 g (89.3% of yield) of 7-amino-3-(1-methyl-1H-tetrazol-5 -yl)thiomethyl-3-cephem-4-carboxylic acid. The NMR values of the product were in accordance with those of the authentic sample.

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling over an external bath at -30° to -20° C.
  3. washrinsing with 0.5 ml of acetonitrile
  4. stirringstirred for 40 minutes
  5. customthe reaction
  6. temperatureThe reaction solution was cooled
  7. customwas placed in a refrigerator overnight
  8. filtrationthe resultant precipitate was recovered by filtration
  9. washwashed with cold water and acetone successively
  10. customdried

Sources & evidence

ORD record
ord-724958eebe5b4a98a1c579349e172ea2
Source dataset
uspto-grants-1984_05
Patent number
US04446318

Linked notes

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