Diethyl Ether → HCID 14456853, compound

HRID 1649761Notes

Reaction equation

HRID 1649761 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[O:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])/[C:27]([O:29]CC)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CCOCC>C(O)C.O1CCOCC1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[O:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])/[C:27]([OH:29])=[O:28])[N:25]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 88475952HCID 88475952, compound

Product 1

HCID 14456853HCID 14456853, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 50 ml of ethanol and 7.1 ml of dioxane is dissolved 4.46 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(4-tert-butoxycarbonylaminobutoxyimino)acetate, followed by addition of 7.1 ml of 2 N-aqueous sodium hydroxide solution. The mixture is stirred at room temperature for 10 hours. To this reaction mixture was added 500 ml of ether and the resulting precipitates are collected by filtration. The precipitate is dissolved in water and under ice-cooling the solution is adjusted to p 2 with 3 N-HCl and extracted with ethyl acetate. The extract is washed with aqueous sodium chloride solution and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. To the residue is added ether-petroleum ether (1:3) and the resulting light yellow powders are collected by filtration. The above procedure yields 4.01 g of 2-(2-tritylaminothiazol-4-yl)-(Z)- 2-(4-tert-butoxycarbonylaminobutoxyimino)acetic acid.

Workup

  1. customthe resulting precipitates
  2. filtrationare collected by filtration
  3. dissolutionThe precipitate is dissolved in water and under ice-
  4. temperaturecooling the solution
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. additionTo the residue is added ether-petroleum ether (1:3)
  10. filtrationthe resulting light yellow powders are collected by filtration

Sources & evidence

ORD record
ord-6ccb42c65b7f488aae43b3fcbffb72ab
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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