Triethylamine → HCID 66650218, compound

HRID 419688Notes

Reaction equation

HRID 419688 reaction equation
Cl.[C:2]([O:6][C:7](=[O:13])[C@H:8]([CH:10]([CH3:12])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[N+:21]([C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Cl)([O-:23])=[O:22]>CCO>[C:2]([O:6][C:7](=[O:13])[C@@H:8]([NH:9][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=1[N+:21]([O-:23])=[O:22])[CH:10]([CH3:11])[CH3:12])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119212-Nitrobenzyl chlorideHCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Product 1

HCID 66650218HCID 66650218, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of valine tert-butyl ester hydrochloride (1.5 g, 7.15 mmol) in EtOH (10 mL) was added triethylamine (2.09 mL, 15 mmol), followed after 10 minutes by 2-nitrobenzyl chloride (1.227 g, 7.15 mmol). The mixture was then stirred for 20 h under reflux before it was evaporated. The residue was purified by flash chromatography (petrol/ethyl acetate, 85/15) to afford the sub-title compound as a colorless oil (1.753 g, 80%). 1H NMR (400 MHz CDCl3) δ 0.93 (6H, m), 1.48 (9H, s), 1.83-1.96 (2H, m), 2.82 (1H, d), 3.92 (1H, d), 4.11 (1H, d), 7.39 (1H, t), 7.57 (1H, t), 7.65 (1H, d), 7.89 (1H, d).

Workup

  1. temperatureunder reflux before it
  2. customwas evaporated
  3. customThe residue was purified by flash chromatography (petrol/ethyl acetate, 85/15)

Sources & evidence

ORD record
ord-efef0edf2b98463aaa7797f84565cf6a
Source dataset
uspto-grants-2012_01
Patent number
US08093392B2

Reaction notes

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