Water → HCID 57738877, compound

HRID 1715736Notes

Reaction equation

HRID 1715736 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:10]([C:11]([O:13]CC)=[O:12])=[C:9]2[O:16][CH2:17][CH2:18][CH2:19][O:20][C:8]2=[C:7]1[C:21]([O:23]CC)=[O:22])C.O.[OH-].[K+]>CC(C)=O>[C:4]([CH2:5][N:6]1[C:7]([C:21]([OH:23])=[O:22])=[C:8]2[O:20][CH2:19][CH2:18][CH2:17][O:16][C:9]2=[C:10]1[C:11]([OH:13])=[O:12])([OH:26])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57738866HCID 57738866, compound

Product 1

HCID 57738877HCID 57738877, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 100-mL round-bottom flask was added diethyl 7-(2-ethoxy-2-oxoethyl)-2,3,4,7-tetrahydro-[1,4]dioxepino[2,3-c]pyrrole-6,8-dicarboxylate (17.56 g, 47.5 mmol), DI water (45 mL), acetone (25 mL), and potassium hydroxide (13.34 g, 238 mmol). The reaction mixture was bubbled with argon for 20 minutes, then refluxed for 2.5 hours, resulting in a deep brown solution. The organic volatiles were removed in vacuo and the remaining aqueous layer was chilled in an ice bath. To the mixture was added concentrated sulfuric acid until a pH of 6 was reached, whereupon a white solid precipitate formed. This precipitate was filtered from the red aqueous solution and washed with several portions of DI water, and after drying weighed 13.55 g (100%). To confirm the structure NMR analysis was performed on the fully deprotonated version by dissolving into a NaOD/D2O solution. 1H NMR (300 MHz, D2O/NaOD): δ 5.17 (s, 2H), 4.13-4.09 (m, 4H), 2.19 (p, 2H, J=5.7 Hz). 13C NMR (75 MHz, CDCl3): δ 180.9, 171.0, 141.9, 120.3, 74, 9, 51.9, 36.3. The product was used in the subsequent reaction without further purification.

Workup

  1. customThe reaction mixture was bubbled with argon for 20 minutes
  2. temperaturerefluxed for 2.5 hours
  3. customresulting in a deep brown solution
  4. customThe organic volatiles were removed in vacuo
  5. temperaturethe remaining aqueous layer was chilled in an ice bath
  6. additionTo the mixture was added concentrated sulfuric acid until a pH of 6
  7. customformed
  8. filtrationThis precipitate was filtered from the red aqueous solution
  9. washwashed with several portions of DI water
  10. customafter drying
  11. dissolutionby dissolving into a NaOD/D2O solution
  12. customThe product was used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-5464c38f871141a3b71487f76dc4a710
Source dataset
uspto-grants-2010_09
Patent number
US07799932B2

Reaction notes

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