Sodium Hydroxide → tert-butyl(2S,3S)-2-[(2-aminoethyl)amino]-3-methylpentanoate

HRID 1174117Notes

Reaction equation

HRID 1174117 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][NH:14][C@@H:15]([C@@H:23]([CH3:26])[CH2:24][CH3:25])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O.NN.[OH-].[Na+]>C(O)C>[NH2:3][CH2:12][CH2:13][NH:14][C@@H:15]([C@@H:23]([CH3:26])[CH2:24][CH3:25])[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 66891692tert-butyl(2S,3S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3-methylpentanoate

Product 1

HCID 86598803tert-butyl(2S,3S)-2-[(2-aminoethyl)amino]-3-methylpentanoateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the product of Example 3F (28.44 g, 78.9 mmol) in ethanol (400 mL) was treated with hydrazine hydrate (25 mL, 789 mmol), stirred at 70° C. for 2 hours, cooled to 25° C. The solid precipitate was dissolved by addition of aqueous NaOH solution (200 mL, 1 N). The reaction was partitioned between dichloromethane and water. The aqueous was extracted three times with dichloromethane. The combined organic extracts were dried over MgSO4, filtered and concentrated to give the title compound (15.4 g, 85% yield), which was used without further purification.

Workup

  1. temperaturecooled to 25° C
  2. customThe reaction was partitioned between dichloromethane and water
  3. extractionThe aqueous was extracted three times with dichloromethane
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0ae2f65e98af490996f553c047726d88
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…