Pyridine → HCID 25199485, compound

HRID 1594639Notes

Reaction equation

HRID 1594639 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%

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 9 (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-1f78eb2b4e0e4000807cd2b216b66d2c
Source dataset
uspto-grants-2001_09
Patent number
US06284767B1

Reaction notes

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