Isobutylamine → N1-Isobutyl-L-alaninamide

HRID 348860Notes

Reaction equation

HRID 348860 reaction equation
C([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])(OC(C)(C)C)=O.[CH2:14]([NH2:18])[CH:15]([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH2:14]([NH:18][C:11](=[O:13])[C@H:9]([CH3:10])[NH2:8])[CH:15]([CH3:17])[CH3:16]

Participants

8

Reactant 4

HCID 6558IsobutylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 13750006N1-Isobutyl-L-alaninamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-L-alanine (5.0 g, 26.4 mmol), isobutylamine (2.9 mL, 29.1 mmol), diisopropylethylamine (11.5 mL, 66 mmol), and HOBt (3.6 g, 26.4 mmol) in anhydrous DMF (15 mL) is stirred 15 min. EDC is added, and the reaction is stirred at room temperature 16 h. The reaction is diluted in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The residue is redissolved in 4N hydrochloric acid in dioxane (30 mL) and stirred for 2 h. The solution is concentrated under reduced pressure, dissolved in chloroform and washed with 1 N NaOH (aq). The aqueous layer is extracted with chloroform, and the pooled organics are dried (sodium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 145.2 [M+H]+.

Workup

  1. washwashed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is redissolved in 4N hydrochloric acid in dioxane (30 mL)
  6. stirringstirred for 2 h
  7. concentrationThe solution is concentrated under reduced pressure
  8. dissolutiondissolved in chloroform
  9. washwashed with 1 N NaOH (aq)
  10. extractionThe aqueous layer is extracted with chloroform
  11. dry with materialthe pooled organics are dried (sodium sulfate)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ceb16366c2c043dc9f7c26730b560e16
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

Loading…