Tetrahydrofuran → HCID 19854502, compound

HRID 1649760Notes

Reaction equation

HRID 1649760 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][S:36][CH2:37][C:38]#[N:39])/[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+].O1CCCC1>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][S:36][CH2:37][C:38]#[N:39])/[C:27]([OH:29])=[O:28])[N:25]=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)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14456852HCID 14456852, compound

Product 1

HCID 19854502HCID 19854502, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 40 ml of ethanol and 5 ml of dioxane is suspended 2.78 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-cyanomethylthioethoxyimino)acetate, followed by addition of 5 ml of 2N aqueous sodium hydroxide solution. The mixture is stirred at room temperature for 2 hours, at the end of which time 40 ml of ethanol and 80 ml of tetrahydrofuran are added. The mixture is further stirred at room temperature for 19 hours. The reaction mixture is concentrated under reduced pressure and 500 ml of ether is added to the residue (about 50 ml). The resulting crystals are collected by filtration and washed with ether. The crystals are dissolved in a mixture of water, tetrahydrofuran and ethyl acetate (1:1:2) and the solution is adjusted to pH 2 and shaken. The organic layer is separated, washed with aqueous sodium chloride solution and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and a mixture of ether and petroleum ether (2:1) is added to the residue. The resulting powders are collected by filtration to give 2.14 g of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-cyanomethylthioethoxyimino)acetic acid as light yellow powders.

Workup

  1. additionare added
  2. concentrationThe reaction mixture is concentrated under reduced pressure and 500 ml of ether
  3. additionis added to the residue (about 50 ml)
  4. filtrationThe resulting crystals are collected by filtration
  5. washwashed with ether
  6. dissolutionThe crystals are dissolved in a mixture of water, tetrahydrofuran and ethyl acetate (1:1:2)
  7. stirringshaken
  8. customThe organic layer is separated
  9. washwashed with aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. distillationThe solvent is distilled off under reduced pressure
  12. additiona mixture of ether and petroleum ether (2:1)
  13. additionis added to the residue
  14. filtrationThe resulting powders are collected by filtration

Sources & evidence

ORD record
ord-12395ca89e334f6bae06b999d29ce8ae
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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