Ethyl Acetate → HCID 21845610, compound

HRID 619234Notes

Reaction equation

HRID 619234 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1/[C:27](=[N:33]/[O:34][C:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)/[C:28]([O:30]CC)=[O:29].[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1.O>[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1/[C:27](=[N:33]/[O:34][C:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)/[C:28]([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 88198389ethyl (2Z)-2-[5-methyl-2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetate

Product 1

HCID 21845610HCID 21845610, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 2-(5-methyl-2-tritylaminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate (9.8 g) in dioxane (40 ml) and water (40 ml) was treated with sodium hydroxide (2.75 g). The mixture was allowed to warm to 100° C. The reaction mixture was cooled to room temperature, diluted with water, and filtered to give a precipitate. A suspension of the precipitate in water and ethyl acetate was allowed to pH 2.5, the organic phase was washed with brine and dried with magnesium sulfate. The solvent was removed under reduced pressure to afford (5-methyl-2-tritylaminothiazol-4-yl)-2-(Z)-(trityloxyimino) acetic acid (9.55 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto give a precipitate
  4. washthe organic phase was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9c82cceb44304f55a8a5a3a961010f62
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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