Hydrochloric Acid → HCID 178524649, compound

HRID 615260Notes

Reaction equation

HRID 615260 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[N:12]=[N:13][NH:14][CH:15]=3)[CH2:7][S:8][C@H:3]12.Cl.C(O[CH:25](OCC)[CH2:26][NH:27][C:28]#[N:29])C>COCCOC.O>[NH:29]1[CH:25]=[CH:26][N:27]=[C:28]1[NH:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[N:12]=[N:13][NH:14][CH:15]=3)[CH2:7][S:8][C@H:3]12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 133930082,2-DiethoxyethylcyanamideHCID 178508101HCID 178508101, compound

Product 1

HCID 178524649HCID 178524649, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
51 °C

Procedure

To a suspension of 7-amino-3-(1H-1,2,3-triazol-4-yl)thiomethylceph-3-em-4-carboxylic acid (31.3 g., 0.1 moles) in a mixture of 1,2-dimethyoxyethane (250 ml.) and concentrated HCl (12 ml., 0.138 moles) in water (50 ml.) was added 2,2-diethoxyethylcyanamide (52.05 g., 0.3 moles). The mixture was stirred and heated at 51° C. for 4 hours and the resulting solution was evaporated under reduced pressure to remove the 1,2-dimethoxyethane. The residual oil was diluted with water (250 ml.), the pH of the resulting suspension was adjusted to 4.8 using sodium bicarbonate and then filtered. The filtrate was applied to a column of "Amberlite" XAD-2 (500 ml.) ("Amberlite" is a Trade Mark). The resin was first washed with water (2000 ml.) and then eluted with 40% v/v aqueous methanol. The required fractions were combined and evaporated to dryness to give 7-(imidazol-2-yl)amino-3-(1H-1,2,3-triazol-4-yl)thiomethylceph-3-em-4-carboxylic acid (3.79 g., 10%) having an n.m.r. spectrum identical to the product of Example 5.

Workup

  1. customthe resulting solution was evaporated under reduced pressure
  2. customto remove the 1,2-dimethoxyethane
  3. additionThe residual oil was diluted with water (250 ml.)
  4. filtrationfiltered
  5. washThe resin was first washed with water (2000 ml.)
  6. washeluted with 40% v/v aqueous methanol
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-51defe37262a450f84b4ba35492bb8b5
Source dataset
uspto-grants-1985_02
Patent number
US04497949

Reaction notes

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