Hydrochloric Acid → HCID 86603764, compound

HRID 2376158Notes

Reaction equation

HRID 2376158 reaction equation
[CH2:1]([O:3][C:4](=[O:27])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]([F:26])[C:10]([NH:13][C@@H:14]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)=[N:11][CH:12]=1)[CH3:2].Cl>CCO.O1CCOCC1>[F:26][C:9]1[CH:8]=[C:7](/[CH:6]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:27])[CH:12]=[N:11][C:10]=1[NH:13][C@@H:14]1[CH2:18][CH2:17][NH:16][CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86603765HCID 86603765, compound

Product 1

HCID 86603764HCID 86603764, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
24 °C

Procedure

To an ice-cooled solution of tert-butyl (3R)-3-({5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-3-fluoro-2-pyridinyl}amino)-1-pyrrolidinecarboxylate (11.6 g) in EtOH (70 ml) was added solution of 4N HCl in dioxane (76.4 ml). The mixture was stirred at 24° C. for 3.5 hr, and evaporated under reduced pressure. The residue was poured into a mixture of water and CH2Cl2. The pH of the aqueous layer was adjusted to ca.9 with NaHCO3. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure to give ethyl (2E)-3-{5-fluoro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}acrylate (7.1 g, 83%) as colorless powder.

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue was poured into a mixture of water and CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8351a8b054c74bf899d7bf3742db838e
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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