Trityl chloride → ethyl (2Z)-2-[5-methyl-2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetate

HRID 619233Notes

Reaction equation

HRID 619233 reaction equation
[H-].[Na+].[CH3:3][C:4]1[S:8][C:7]([NH:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1/[C:29](=[N:35]/[OH:36])/[C:30]([O:32][CH2:33][CH3:34])=[O:31].[C:37](Cl)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(OCC)(=O)C>[CH3:3][C:4]1[S:8][C:7]([NH:9][C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[N:6][C:5]=1/[C:29](=[N:35]/[O:36][C:37]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)/[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 88197801HCID 88197801, compound

Product 1

HCID 88198389ethyl (2Z)-2-[5-methyl-2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetateYield 40.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of sodium hydride (1.37 g) in 110 ml of ethyl acetate, ethyl 2-(5-methyl-2-tritylaminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetate (16.15 g) was added at room temperature. The mixture was treated with a solution of trityl chloride (9.55 g) in ethyl acetate (66 ml). After 20 hours, the reaction was quenched by ice-water. The aqueous phase was extracted with ethyl acetate, and the combined extracts were washed with brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel with 5%-17% ethyl acetate/hexane to give 9.8 g of ethyl 2-(5-methyl-2-tritylaminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate.

Workup

  1. additionwas added at room temperature
  2. customthe reaction was quenched by ice-water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel with 5%-17% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d289c50fbd4e45df9066b3ee68383fce
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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