Triethylamine → HCID 68710350, compound

HRID 1927804Notes

Reaction equation

HRID 1927804 reaction equation
Cl.[C:2]([O:6][C:7](=[O:14])[C@H:8]([C@H:10]([CH2:12][CH3:13])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[C:22](Cl)(=[O:31])[C:23]1[C:24]([O:29][CH3:30])=[CH:25][CH:26]=[CH:27][CH:28]=1>C(Cl)Cl>[C:2]([O:6][C:7](=[O:14])[C@@H:8]([NH:9][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[CH:10]([CH3:11])[CH2:12][CH3:13])([CH3:4])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 11687228tert-Butyl isoleucinate--hydrogen chloride (1/1)

Product 1

HCID 68710350HCID 68710350, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Isoleucine tertbutyl ester hydrochloride (500 mg, 2.23 mmol) was dissolved in CH2Cl2 (10 ml). Triethylamine (600 g, 6.0 mmol) and 2-anisoyl chloride (456 mg, 2.68 mmol) were added. After 18 h at room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (100 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 60% Pet. ether, 40% ethyl acetate) to give a colourless oil identified as the title compound (341 mg, 1.06 mmol, 48%).

Workup

  1. customAfter 18 h at room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 60% Pet. ether, 40% ethyl acetate)
  6. customto give a colourless oil

Sources & evidence

ORD record
ord-677ca9e690e04341b730831a62a2892e
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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