Trityl chloride → HCID 88198389, compound

HRID 1274970Notes

Reaction equation

HRID 1274970 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 88198389HCID 88198389, compoundYield 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-6acfca054a9e40fc9f2ca961ed659c21
Source dataset
uspto-grants-2000_12
Patent number
US06159961

Reaction notes

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