N-bromobutanimide → HCID 68291092, compound

HRID 1507969Notes

Reaction equation

HRID 1507969 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:22])[C:10]([C:13]1[O:14][CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[N:17]=1)([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(Br)C(=O)C1>C(Cl)(Cl)(Cl)Cl.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:22])[C:10]([C:13]1[O:14][CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[N:17]=1)([CH3:12])[CH3:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68291876HCID 68291876, compound

Product 1

HCID 68291092HCID 68291092, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 2-((R)-3-((tert-butoxycarbonyl)amino)-2-methylbutan-2-yl)-4,5-dihydrooxazole-4-carboxylate (2.0 g, 6.36 mmol) in CCl4 (180 mL) was added NBS (3.96 g, 22.27 mmol) at RT. The reaction mixture was heated to 85° C. and stirred for 30 min. It was then diluted with water and extracted with CCl4 (3×50 mL). The combined organic layers were dried over anhydrous Na2SO4 and the solvent was removed under vacuum. Crude product was purified by ELSD combiflash (120 g silica column, 40% EtOAc: Pet-Ether) to afford a white solid (1.2 g, 60.4%). 1HNMR (400 MHz, CDCl3) δ ppm: 1.12 (d, J=6.8 Hz, 3H), 1.408 (s, 15H), 3.89-3.97 (m, 4H), 4.88-4.91 (d, J=10 Hz, 1H), 8.17 (s, 1H). LC retention time: 1.985 min (analytical HPLC Method N).

Workup

  1. extractionextracted with CCl4 (3×50 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customthe solvent was removed under vacuum
  4. customCrude product was purified by ELSD combiflash (120 g silica column, 40% EtOAc: Pet-Ether)

Sources & evidence

ORD record
ord-564a266c35b24f17883794c42702d94c
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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