Trityl chloride → HCID 4081485, compound

HRID 354647Notes

Reaction equation

HRID 354647 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:20][O:21][CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:23]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:20][O:21][CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 4081485HCID 4081485, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-35 °C

Procedure

2.9 ml of triethylamine were added at -10° C. to a mixture of 4.6 g of the product of Step A in 92 ml of methylene chloride and after cooling to -35° C., 6.1 g of trityl chloride were added thereto. The temperature was allowed to rise to room temperature in about 21/2 hours and the reaction mixture was washed with water and then with 0.5 N hydrochloric acid and finally with aqueous sodium acetate. The mixture was dried and evaporated to dryness. The residue was taken up in ether and the solution was concentrated to dryness again. The residue was dissolved in methanol and water and ether were added to cause crystallization. The mixture was vacuum filtered and the recovered precipitate was washed with ether to obtain 6.15 g of ethyl 2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetate melting at 120° C. having the syn configuration.

Workup

  1. customto rise to room temperature in about 21
  2. custom2 hours
  3. washthe reaction mixture was washed with water
  4. customThe mixture was dried
  5. customevaporated to dryness
  6. concentrationthe solution was concentrated to dryness again
  7. dissolutionThe residue was dissolved in methanol
  8. additionwater and ether were added
  9. customcrystallization
  10. filtrationfiltered
  11. washthe recovered precipitate was washed with ether

Sources & evidence

ORD record
ord-a9a1a43bf8fa4fd4a47c5cb12b7a3b64
Source dataset
uspto-grants-1983_03
Patent number
US04376203

Reaction notes

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