Hydrazine hydrate (1:1) → HCID 11411236, compound

HRID 2066003Notes

Reaction equation

HRID 2066003 reaction equation
[C:1]([O:5][C:6](=[O:56])[N:7]([CH2:22][CH2:23][CH2:24][N:25]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:26][CH2:27][CH2:28][CH2:29][N:30]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:8][CH2:9][CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[C:1]([O:5][C:6](=[O:56])[N:7]([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:22][CH2:23][CH2:24][N:25]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:26][CH2:27][CH2:28][CH2:29][N:30]([C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67211640HCID 67211640, compound

Product 1

HCID 11411236HCID 11411236, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound from Stage 2 above (1.49 g, 1.88 mmol, 1 eq) is refluxed in 50 mL of EtOH in the presence of hydrazine hydrate (0.5 mL, 16.1 mmol, 8.5 eq) for 6 hrs. The cooled medium is filtered, washed with EtOH, and evaporated. The residue is flash chromatographed on SiO2 (gradient elution pure CH2Cl2 up to 80:18:2 CH2Cl2:MeOH:NH4OH). After evaporation of the pure fractions, 1.09 g of a colorless oil is obtained (yield 88%). TLC SiO2 (90:9:1 CH2Cl2:MeOH:NH4OH) Rf=0.34. MS: m/z=660 (M-H+).

Workup

  1. filtrationThe cooled medium is filtered
  2. washwashed with EtOH
  3. customevaporated
  4. customchromatographed on SiO2 (gradient elution pure CH2Cl2 up to 80:18:2 CH2Cl2:MeOH:NH4OH)
  5. customAfter evaporation of the pure fractions

Sources & evidence

ORD record
ord-158823f02ceb423086cb596140a3e559
Source dataset
uspto-grants-2012_10
Patent number
US08288567B2

Reaction notes

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