Triethylamine → HCID 178501494, compound

HRID 2387716Notes

Reaction equation

HRID 2387716 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[Br:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl.[CH3:24][O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:31])[CH3:30])[NH2:28]>>[CH3:24][O:25][C:26](=[O:32])[C@@H:27](/[N:28]=[CH:14]/[C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:7])[N:13]=1)[CH:29]([CH3:31])[CH3:30]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 111190Methyl valinate hydrochlorideHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 178501494HCID 178501494, compound

Procedure

Anhydrous magnesium sulfate (5.4 g), 6-bromopyridine-2-carboxaldehyde (5.0 g, 26.9 mmol) and triethylamine (3.75 mL, 26.9 mmol) were each added sequentially in one portion to a cooled (0° C.) solution of (L)-valine methyl ester hydrochloride (4.51 g, 26.9 mmol) and the reaction mixture was allowed to warm slowly to room temperature overnight under a nitrogen atmosphere. The mixture was then filtered and the filter cake washed with diethyl ether (100 mL) before evaporating the filtrate in vacuo. The residue was purified by column chromatography using 5:1 hexane/ethyl acetate as eluent to yield A469.1 (7.1 g, 88%). HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 0.86 min, M+H+=202.08

Workup

  1. additioneach added sequentially in one portion to
  2. filtrationThe mixture was then filtered
  3. washthe filter cake washed with diethyl ether (100 mL)
  4. custombefore evaporating the filtrate in vacuo
  5. customThe residue was purified by column chromatography
  6. customto yield A469.1 (7.1 g, 88%)
  7. custom4.6×33 mm (2 min grad)

Sources & evidence

ORD record
ord-fc02ca886fc9497b9fab488cb7741a3c
Source dataset
uspto-grants-2012_09
Patent number
US08268855B2

Reaction notes

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