Tert-Butylamine → 4-(tert-Butylamino)-4-oxobutanoic acid

HRID 2236013Notes

Reaction equation

HRID 2236013 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]([NH2:12])([CH3:11])([CH3:10])[CH3:9]>ClCCl>[C:8]([NH:12][C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7922Succinic anhydride

Product 1

HCID 2450094-(tert-Butylamino)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.07 g (30.6 mmol) of succinic anhydride was suspended in 30 ml of dichloromethane. 4.1 ml (34.5 mmol) of t-butylamine was dropped into the suspension, and the resultant mixture was stirred at room temperature for 1 hour. White crystals thus formed were washed with ethyl acetate and then dissolved in 40 ml of 1 N aqueous sodium hydroxide solution. The resultant solution was stirred at room temperature for 2 hours and then acidified with 1 N aqueous hydrochloric acid solution under cooling with ice. After extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. customWhite crystals thus formed
  2. washwere washed with ethyl acetate
  3. dissolutiondissolved in 40 ml of 1 N aqueous sodium hydroxide solution
  4. temperatureunder cooling with ice
  5. extractionAfter extracting with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-353b91e604dc4cad8f8947cad071e2d4
Source dataset
uspto-grants-2010_05
Patent number
US07713957B2

Reaction notes

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