Pyridine → HCID 25199485, compound

HRID 1180124Notes

Reaction equation

HRID 1180124 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH2:5].N1C=CC=CC=1.[Br:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH:5][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][Br:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 702254-Bromobutyryl chlorideHCID 94285Valine methyl ester

Product 1

HCID 25199485HCID 25199485, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.08 g (8.4 mmole) of L-valine methyl ester in 30 ml of CH2Cl2 was added 1.36 ml (16.8 mmole) of pyridine, cooled to 0° C. and 1.55 g (8.4 mmole) of 4-bromobutanoyl chloride added. The solution was stirred at 0° C. for 40 minutes and at RT for 1 h. The solution was washed with satd. NaHCO3, brine and dried with anhy. Na2SO4; filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (5% EtOAc/CH2Cl2) to provide 1.82 g (77%) of desired product. 300 MHz 1H NMR (CDCl3) δ 0.92 (d, J=6 Hz, 3H), 0.96 (d, J=6 Hz, 3H) 2.20 (m, 3H), 2.46 (m, 2H), 3.50 (m, 2H), 3.76 (s, 3H), 4.58 (dd, J=4,7 Hz, 1H), 5.97 (br d, J=7 Hz, 1H). Mass spectrum: (M+H)+=297.

Workup

  1. washThe solution was washed with satd
  2. dry with materialNaHCO3, brine and dried with anhy
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel column chromatography (5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-cee00fee53a64ed99dbdacef0e1bd180
Source dataset
uspto-grants-2007_10
Patent number
US07279582B2

Reaction notes

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