N-bromobutanimide → HCID 86651794, compound

HRID 241275Notes

Reaction equation

HRID 241275 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:31])C(=O)C1>C(#N)C>[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([C:9]1[CH:14]=[CH:13][C:12]([Br:31])=[C:11]([CH3:15])[N:10]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86651793N-[(1,1-Dimethylethoxy)carbonyl]-N-(6-methyl-2-pyridinyl)glycine 1,1-dimethylethyl ester

Product 1

HCID 86651794HCID 86651794, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl[tert-butoxycarbonyl(6-methylpyridin-2-yl)amino]-acetate (477 mg, 1.48 mmol) obtained in Reference Example 1-(a) in acetonitrile (3 ml) was added NBS (398 mg, 2.24 mmol), followed by stirring at 40° C. for 3 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=20:1→5:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (565 mg) as a white solid. (Yield: 95%)

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additioncontaining the desired compound
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-49f60a2e8eb54faca7888e18edfb076d
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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