Hydrazine hydrate (1:1) → (+/-)-Tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

HRID 877226Notes

Reaction equation

HRID 877226 reaction equation
[CH:1]1([CH:6]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:33]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:28][CH:27]=2)[C:7]([NH:9][C:10]2[C:11]([CH3:25])=[C:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>C(O)C>[NH2:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([CH:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:7]([NH:9][C:10]2[C:11]([CH3:25])=[C:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58136374tert-Butyl(+/-)-3-(3-(2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetamido)-2-methylphenyl)propanoate

Product 1

HCID 58136676(+/-)-Tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.5 g (14.6 mmol) of tert-butyl(+/−)-3-(3-(2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetamido)-2-methylphenyl)propanoate were initially charged in 85 ml of ethanol, and 2.35 ml (48.3 mmol) of hydrazine hydrate were added. The reaction mixture was heated under reflux overnight. After cooling to room temperature, the precipitated solid was filtered off and washed with ethanol. The filtrate was concentrated, the residue was triturated with acetonitrile and the precipitated crystals were filtered off with suction and discarded. The mother liquor was concentrated and the residue was purified by flash chromatography on silica gel (mobile phase dichloromethane/methanol/aq. ammonia 100:5:1). This gave 4.51 g (68% of theory) of the target compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated
  6. customthe residue was triturated with acetonitrile
  7. filtrationthe precipitated crystals were filtered off with suction
  8. concentrationThe mother liquor was concentrated
  9. customthe residue was purified by flash chromatography on silica gel (mobile phase dichloromethane/methanol/aq. ammonia 100:5:1)

Sources & evidence

ORD record
ord-506bd1d3fd43422f9b8cd230ad7a43b1
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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