Water → HCID 54040437, compound

HRID 2081740Notes

Reaction equation

HRID 2081740 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@@H:3]1[S:4][C@@:5]([N:13]1[CH2:17][CH2:16][N:15]([N:18]=[CH:19]C3C=CC=CC=3)[C:14]1=[O:26])([C:10]([OH:12])=[O:11])[CH2:6]2.Cl.[N+](C1C=C([N+]([O-])=O)C=CC=1NN)([O-])=O.[OH2:42].O.[NH3:44]>CO>[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@@H:3]1[S:4][C@:5]([C:10]([OH:12])=[O:11])([N:13]1[CH2:17][CH2:16][N:15]([NH:18][C:19]([NH2:44])=[O:42])[C:14]1=[O:26])[CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 54633122,4-Dinitrophenylhydrazinium(1+) chlorideHCID 12896473Azane;hydrateHCID 54107732HCID 54107732, compound

Product 1

HCID 54040437HCID 54040437, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 150 ml of methanol was suspended 10.0 g of (3R,5R,6R)-6-amino-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-3-carboxy-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane. Thereto was added 9.2 g of 2,4-dinitrophenylhydrazine hydrochloride at 20°-25° C. The mixture was stirred at the same temperature for 3 hours. 100 ml of water was added to the reaction mixture. The mixture was adjusted to pH 8.0 with concentrated ammonia water. The resulting crystals were removed by filtration. To the filtrate was slowly added concentrated hydrochloric acid to adjust the filtrate to pH 1.5. To the filtrate was added 2.5 g of active carbon, and the mixture was stirred at room temperature for 5 minutes. The active carbon was removed by filtration and washed with water. The filtrate and washings were combined and to the resulting mixture was added 3.9 g of sodium cyanate at room temperature in 60 minutes while maintaining the reaction mixture at pH 1.6 to 2.1 with concentrated hydrochloric acid. After the addition, the mixture was stirred at room temperature for 60 minutes. The resulting crystals were collected by filtration and suspended in 50 ml of water. To the suspension was added concentrated ammonia water to adjust the suspension to pH 9.0. Then, 0.4 g of active carbon was added, and the mixture was stirred at room temperature for 5 minutes. The active carbon was removed by filtration and washed with water. Concentrated hydrochloric acid was added to a mixture of the washings and the previously obtained filtrate to adjust the pH to 4.5. The mixture was stirred at room temperature for 30 minutes. The resulting crystals were collected by filtration, washed with water and acetone in this order, and dried under reduced pressure to obtain 5.81 g (yield: 66.0%) of (3R,5R,6R)-6-amino-3-carboxy-7-oxo-3-(2-oxo-3-ureidoimidazolidin-1-yl)-4-thia-1-azabicyclo[3.2.0]heptane.

Workup

  1. customThe resulting crystals were removed by filtration
  2. additionTo the filtrate was slowly added concentrated hydrochloric acid
  3. additionTo the filtrate was added 2.5 g of active carbon
  4. stirringthe mixture was stirred at room temperature for 5 minutes
  5. customThe active carbon was removed by filtration
  6. washwashed with water
  7. additionwas added 3.9 g of sodium cyanate at room temperature in 60 minutes
  8. temperaturewhile maintaining the reaction mixture at pH 1.6 to 2.1 with concentrated hydrochloric acid
  9. additionAfter the addition
  10. stirringthe mixture was stirred at room temperature for 60 minutes
  11. filtrationThe resulting crystals were collected by filtration
  12. additionTo the suspension was added concentrated ammonia water
  13. additionThen, 0.4 g of active carbon was added
  14. stirringthe mixture was stirred at room temperature for 5 minutes
  15. customThe active carbon was removed by filtration
  16. washwashed with water
  17. additionConcentrated hydrochloric acid was added to a mixture of the washings
  18. stirringThe mixture was stirred at room temperature for 30 minutes
  19. filtrationThe resulting crystals were collected by filtration
  20. washwashed with water and acetone in this order
  21. customdried under reduced pressure

Sources & evidence

ORD record
ord-b15b790a2f2941179f7f99900002f7b8
Source dataset
uspto-grants-1993_02
Patent number
US05185330

Reaction notes

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