Isobutylamine → N2-(tert-butoxycarbonyl)-N1-isobutyl-L-alaninamide

HRID 1062902Notes

Reaction equation

HRID 1062902 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([NH2:30])[CH:27]([CH3:29])[CH3:28]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:30][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:13])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 682631,1'-CarbonyldiimidazoleHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 28168390N2-(tert-butoxycarbonyl)-N1-isobutyl-L-alaninamideYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-tert-Butoxycarbonylalanine (2.8 g, 15 mmol) and carbonyldiimidazole (2.75 g, 17 mmol) are stirred together in 30 mL of dry THF under nitrogen for 1 h. To this is added 3 mL (30 mmol) of isobutyl amine, and the mixture is stirred for one week. It is then concentrated, dissolved in ethyl acetate, and washed successively with 1 N KHSO4, water, and brine, and dries over Na2SO4. Concentration affords the title compound as a white solid (2.25 g, 9.2 mmol, 62%). 1H NMR (CDCl3) δ 6.27 (m, 1H), 5.02 (m, 1H), 4.13 (m, 1H), 3.08 (m, 2H), 1.77 (m, 1H), 1.45 (s, 9H), 1.35 (d, J=7 Hz, 3H), 0.90 (d, J=7 Hz, 6H).

Workup

  1. concentrationIt is then concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed successively with 1 N KHSO4, water, and brine, and dries over Na2SO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-46c46dfea0e443ff9ee870101991e243
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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