Hydrazine hydrate (1:1) → HCID 57435093, compound

HRID 1366906Notes

Reaction equation

HRID 1366906 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:19])[C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[NH:3][N:2]=1)=[O:19])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57435092HCID 57435092, compound

Product 1

HCID 57435093HCID 57435093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.41 mL, 8.48 mmol) was added to a stirring room temperature solution of 49 (0.1.9190 g, 8.48 mmol) in EtOH (8.5 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by HPLC (½ h): The reaction was concentrated and purified by silica gel chromatography (Combiflash column, 96:4 Hexanes:2N NH3 in EtOH): 1H (CDCl3, 400 MHz): δ 12.73 (1H, broad s), 6.57 (1H, s), 5.09 (1H, t, J=6.8 Hz), 4.32 (2H, q, J=7.1 Hz), 2.70 (2H, t, J=7.5 Hz), 2.29 (2H, q, J=7.5 Hz), 1.63 (3H, s), 1.52 (3H, s), 1.30 (3H, t, J=7.1 Hz) ppm. Partial 13C (CDCl3, 100 MHz): δ 162.27, 106.11, 60.65, 31.49, 27.53, 25.52, 17.51, 13.10 ppm. HPLC: 9.986 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. customuntil judged complete by HPLC (½ h)
  4. concentrationThe reaction was concentrated
  5. custompurified by silica gel chromatography (Combiflash column, 96:4 Hexanes:2N NH3 in EtOH)
  6. custom9.986 min.

Sources & evidence

ORD record
ord-dd0e216957494bf0b04a7143e0c52eb3
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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