Hydrochloric Acid → HCID 53889719, compound

HRID 1904125Notes

Reaction equation

HRID 1904125 reaction equation
[OH:1][N:2]=[C:3]([C:7]1[N:8]=[C:9]([NH:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:10][CH:11]=1)[C:4]([OH:6])=[O:5].C[N:33]([CH3:36])C=O.[C:37](#[N:39])[CH3:38].Cl.[C:41](OCC)(=O)C>O>[C:37]([CH2:38][O:1][N:2]=[C:3]([C:7]1[N:8]=[C:9]([NH:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:10][CH:11]=1)[C:4]([O:6][CH2:41][C:36]#[N:33])=[O:5])#[N:39]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 730781342-(2-Tritylamino-4-thiazolyl)-2-hydroxyimino-acetic acid

Product 1

HCID 53889719HCID 53889719, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.9 g of the syn isomer of 2-(hydroxyimino)-2-(2-tritylamino-4-thiazolyl)-acetic acid, 60 ml of dry dimethylformamide and 7.6 ml of acetonitrile was stirred under an inert atmosphere until the mass solidified and the mixture stood for 65 hours in a closed atmosphere. The mass was poured into a mixture of 750 ml of water, 130 ml of N hydrochloric acid and 150 ml of ethyl acetate and the mixture was stirred and was vacuum filtered. The filter was rinsed with ethyl acetate and with water and the decanted organic phase was washed with 100 ml of water. The wash water was extracted 3 times with 100 ml of ethyl acetate. The combined organic phases were dried and vacuum filtered. The filter was rinsed and the filtrate was evaporated to dryness. The residue was chromatographed over silica gel and elution with ether. The ether was evaporated to obtain 8.69 g of the syn isomer of cyanomethyl 2-(cyanomethyloxyimino)-2-(2-tritylamino-4-thiazolyl)-acetate in the form of an oil.

Workup

  1. stirringthe mixture was stirred
  2. filtrationfiltered
  3. washThe filter was rinsed with ethyl acetate and with water
  4. washthe decanted organic phase was washed with 100 ml of water
  5. extractionThe wash water was extracted 3 times with 100 ml of ethyl acetate
  6. customThe combined organic phases were dried
  7. filtrationvacuum filtered
  8. washThe filter was rinsed
  9. customthe filtrate was evaporated to dryness
  10. customThe residue was chromatographed over silica gel and elution with ether
  11. customThe ether was evaporated

Sources & evidence

ORD record
ord-f12002c8c3fc4ccdb8b75438cfb8fb6a
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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