Isobutylamine → HCID 28165295, compound

HRID 1062891Notes

Reaction equation

HRID 1062891 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:28]([NH2:32])[CH:29]([CH3:31])[CH3:30]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:32][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:15])[CH:10]([CH3:11])[CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 682631,1'-CarbonyldiimidazoleHCID 83693Boc-L-Valine

Product 1

HCID 28165295HCID 28165295, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-t-butoxycarbonylvaline (2.2 g, 10 mmol) is dissolved in, dry THF under nitrogen, and to this is added 2.0 g (12 mmol) of carbonyldiimidazole. After this mixture is stirred for 50 min, 2.0 mL (20 mmol) of isobutylamine is added. After 1 week, the mixture is concentrated, dissolved in ethyl acetate, and washed successively with aqueous potassium hydrogen sulfate, water, and brine. It is dried over anhydrous sodium sulfate and concentrated to 2.27 g (8.3 mmol, 83%) of the title compound as a white solid. NMR (CDCl3) δ 6.0 (br, 1H), 5.07 (br d, 1H), 3.83 (m, 1H), 3.10 (m, 2H), 2.14 (m, 1H), 1.77 (m, 1H), 1.44 (s, 9H), 1.01-0.90 (overlapping d, 12H). HRMS (ESI) calcd for C14H28N2O3+H1 273.2178, found 273.2180

Workup

  1. waitAfter 1 week
  2. concentrationthe mixture is concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed successively with aqueous potassium hydrogen sulfate, water, and brine
  5. dry with materialIt is dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-4c214dea7c714d53ad85a22ccf0398d8
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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