Hydrochloric Acid → HCID 53722240, compound

HRID 851825Notes

Reaction equation

HRID 851825 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].Cl.[C:8]([NH:27][C:28]1[S:29][CH:30]=[C:31]([C:33](=[N:39][OH:40])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:32]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.BrCC(O[CH2:46][CH3:47])=O.[CH3:48]N(C)C=O>C(OCC)(=O)C.O>[C:8]([NH:27][C:28]1[S:29][CH:30]=[C:31]([C:33](=[N:39][O:40][CH:48]([CH2:46][CH3:47])[C:1]([OH:2])=[O:4])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:32]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

Product 1

HCID 53722240HCID 53722240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.28 g of pure potassium carbonate were added under argon to a mixture of 9.88 g of the hydrochloride of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetate in 25 ml of dry dimethylformamide and the mixture was stirred for 15 minutes and was then cooled for 10 minutes on a methanol-ice bath. 11.2 ml of ethyl bromacetate were added dropwise over 5 minutes and spontaneous heating occurred with stirring under an inert atmosphere. The mixture was poured into a mixture of 400 ml of water and 80 ml of ethyl acetate and the mixture was stirred and decanted. The organic phase was washed twice with 80 ml of water and the aqueous phase was extracted with 80 and 50 ml of ethyl acetate. The organic phase was dried and vacuum filtered. The filter was rinsed and the filtrate was evaporated to dryness. The residue was taken up in ether and the mixture was stirred while crystallization occured. The mixture was vacuum filtered and the product was rinsed with ether and dried to obtain 7.54 g of syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-(ethylcarboxymethyloxyimino)-acetate melting at 154° C. RMN (CDCl3 - 60 MHz): 4.75 ppm (O--CH2 --COO); 6.55 ppm (proton of thiazole ring).

Workup

  1. temperaturewas then cooled for 10 minutes on a methanol-ice bath
  2. temperaturespontaneous heating
  3. stirringwith stirring under an inert atmosphere
  4. stirringthe mixture was stirred
  5. customdecanted
  6. washThe organic phase was washed twice with 80 ml of water
  7. extractionthe aqueous phase was extracted with 80 and 50 ml of ethyl acetate
  8. customThe organic phase was dried
  9. filtrationvacuum filtered
  10. washThe filter was rinsed
  11. customthe filtrate was evaporated to dryness
  12. stirringthe mixture was stirred while crystallization
  13. filtrationfiltered
  14. washthe product was rinsed with ether
  15. customdried

Sources & evidence

ORD record
ord-42c2929cf7654fe885281f6baf7e1f67
Source dataset
uspto-grants-1983_05
Patent number
US04386210

Reaction notes

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