HCID 12870305, compound → AC1L7QBR

HRID 654261Notes

Reaction equation

HRID 654261 reaction equation
[C:1]([C@H:4]1[C@@H:9]([C:10](=[O:12])[NH2:11])[N:8]([CH2:13][C:14](OCC)=[O:15])[CH2:7][CH2:6][N:5]1[CH2:19][C:20]([O:22]CC)=O)(=[O:3])[NH2:2]>CCO.CC[O-].[Na+]>[C:1]1(=[O:3])[C@H:4]2[C@H:9]3[C:10](=[O:12])[NH:11][C:14](=[O:15])[CH2:13][N:8]3[CH2:7][CH2:6][N:5]2[CH2:19][C:20](=[O:22])[NH:2]1

Participants

4

Reactant 1

HCID 12870305HCID 12870305, compound

Product 1

HCID 339587AC1L7QBR

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

Method A. The diester diamide 11 (0.65 g, 1.88 mmol) was added to a solution of Na (0.173 g) in 7 mL of absolute EtOH at room temperature under argon. The resulting suspension in NaOEt was heated at 85° C. for 6 hours, during which time the reaction mixture became turbid. Following stirring at room temperature for 14 hours, the solvent was removed under reduced pressure, and the residual solid was dissolved in 3 mL of H2O. The aqueous solution was acidified (concentrated HCl, pH 2), and the crystalline compound obtained upon cooling in the refrigerator was filtered, washed with 5 mL of cold H2O followed by 5 mL of ethanol, and dried: yield 0.333 g (70%); mp 282°-284° C. dec. This compound was identical in all respects with the cis tricyclic compound 2 prepared from diamide 7 as previously described.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residual solid was dissolved in 3 mL of H2O
  3. customthe crystalline compound obtained
  4. temperatureupon cooling in the refrigerator
  5. filtrationwas filtered
  6. washwashed with 5 mL of cold H2O
  7. customdried
  8. customprepared from diamide 7

Sources & evidence

ORD record
ord-f5caa09cb2bf45d39f40d458f4b87c8b
Source dataset
uspto-grants-1992_07
Patent number
US05130426

Reaction notes

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