Hydrazine hydrate (1:1) → HCID 57561711, compound

HRID 1366909Notes

Reaction equation

HRID 1366909 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:24])[C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH2:12][CH:13]1[CH:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]1([CH3:21])[CH3:20])[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][CH:13]2[CH:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]2([CH3:21])[CH3:20])[NH:3][N:2]=1)=[O:24])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57435094HCID 57435094, compound

Product 1

HCID 57561711HCID 57561711, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.867 mL, 17.9 mmol) was added to a stirring room temperature solution of 52 (5.2981 g, 17.9 mmol) in EtOH (17.9 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by HPLC. The reaction was concentrated and purified by silica gel chromatography (Combiflash column, 97:3 Hexanes:2N NH3 in EtOH) to obtain 1.6604 g (31.8%) of 53. Partial 1H (CDCl3, 400 MHz): δ 12.45 (1H, broad s), 6.58 (1H, s), 4.32 (2H, q, J=7.1 Hz), 2.63 (2H, t, J=8.3 Hz), 1.31 (3H, t, J=7.1 Hz), 0.90 (3H, s), 0.83 (3H, s), 0.78 (3H, d, J=6.8 Hz) ppm. Partial 13C (CDCl3, 100 MHz): δ 106.04, 60.66, 48.99, 34.03, 30.10, 24.89, 14.17 ppm. HPLC: 12.000 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated
  4. custompurified by silica gel chromatography (Combiflash column, 97:3 Hexanes:2N NH3 in EtOH)

Sources & evidence

ORD record
ord-761026025d6842138febaa1f9c464ed6
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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