1-Bromo-3-methylbutane → HCID 60098544, compound

HRID 1882916Notes

Reaction equation

HRID 1882916 reaction equation
Br[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9](=[O:25])[C@H:10]([CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:15]([O:14][C:12]([NH:11][C@@H:10]([CH2:19][C:20]1[N:24]=[CH:23][N:22]([CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])[CH:21]=1)[C:9]([O:8][CH3:7])=[O:25])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 10340Sodium CarbonateHCID 178501431HCID 178501431, compound

Product 1

HCID 60098544HCID 60098544, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromo-3-methylbutane (4.44 ml, 37.2 mmol) was added to a mixture of Nα-Boc-L-histidine methyl ester (5.0 g, 18.6 mmol) and sodium carbonate (4.0 g, 37.2 mmol) in acetonitrile (80 ml), and the mixture was heated under reflux for 18 hours. The cooled mixture was concentrated under reduced pressure. The residue was suspended in water and the suspension was basified using sodium carbonate then extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried (Na2SO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of hexane:ethyl acetate (100:0 to 5:95) to afford the title compound as a colourless oil, 2.8 g. 1H-NMR (CDCl3, 400 MHz) δ: 0.90 (d, 6H), 1.40 (s, 9H), 1.50 (m, 1H), 1.60 (m, 2H), 2.96-3.06 (m, 2H), 3.62 (s, 3H), 3.82 (t, 2H), 4.50 (m, 1H), 5.85 (m, 1H), 6.62 (s, 1H), 7.32 (s, 1H). LRMS: m/z (ES+) 340 [MH+]. [α]D=−2.3 (c=0.22, methanol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. extractionthen extracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residual oil was purified by column chromatography on silica gel using an elution gradient of hexane:ethyl acetate (100:0 to 5:95)

Sources & evidence

ORD record
ord-b0d851b38c1a4047b8ad4f6065e8e457
Source dataset
uspto-grants-2004_07
Patent number
US06759426B2

Reaction notes

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