tert-Butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazine-1-carboxylate → HCID 86602021, compound

HRID 1865408Notes

Reaction equation

HRID 1865408 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([NH:14][NH:15]C(OC(C)(C)C)=O)[CH3:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)[Cl:31].C([SiH](C(C)C)C(C)C)(C)C>>[Cl-:31].[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([NH2+:14][NH2:15])[CH3:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 67482189tert-Butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazine-1-carboxylateHCID 131724618HCID 131724618, compound

Product 1

HCID 86602021HCID 86602021, compound

Procedure

tert-Butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate (29 g, 94 mmol) was treated with 100 ml of TFA-DCM-triisopropylsilane (20:20:1) at room temperature for one hour. The mixture was concentrated under reduced pressure, and the residue was dissolved in water (100 ml), washed with DCM 2×. The DCM was back extracted with water 3×. HCl (5N, 20 ml) was added to the combined water solution and concentrated to ˜50 ml. CH3CN (50 ml) was added and this was lyophilized to yield {1-[4-(ethoxycarbonyl)phenyl]ethyl}-hydrazinium chloride. NMR (500 MHz, acetone-d6) δ: 1.34 (t, J=7.1 Hz, 3H); 1.67 (d, J=6.8 Hz, 3H); 4.33 (q, J=7.1 Hz, 2H), 4.97 (q, J=6.8 Hz, 1H), 7.76 (d, J=8.5 Hz, 2H), 7.97 (d, J=8.5 Hz, 2H). MS C11H16N2O2 Cald: 208.12; Obsd (M+1): 209.19.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water (100 ml)
  3. washwashed with DCM 2×
  4. extractionThe DCM was back extracted with water 3×
  5. additionHCl (5N, 20 ml) was added to the combined water solution
  6. concentrationconcentrated to ˜50 ml
  7. additionCH3CN (50 ml) was added

Sources & evidence

ORD record
ord-969e590499934ba48670d718055bbc08
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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