Sodium hydride → HCID 86604577, compound

HRID 131415Notes

Reaction equation

HRID 131415 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[H][H].Br[CH2:20][C:21]([CH3:23])=[CH2:22].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:3]([O:7][C:8]([NH:10][C@H:11]([CH2:12][O:13][CH2:22][C:21]([CH3:23])=[CH2:20])[C:14]([OH:16])=[O:15])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 3577853-Bromo-2-methyl-1-propeneHCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, compound

Product 1

HCID 86604577HCID 86604577, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Wash a 60% dispersion of sodium hydride in mineral oil (4.4 g, 115 mmol) with hexanes. Add DMF (30 mL), and cool in an ice bath. Add dropwise a solution N-(tert-butoxycarbonyl)-L-serine (10.0 g, 49 mmol) in DMF (160 mL). Warm to room temperature and stir until hydrogen evolution ceases after one hour. Cool in an ice bath and add 3-bromo-2-methyl-propene (7.40 g, 55 mmol). Stir for 2 hours. Pour mixture onto 5% aqueous sodium bicarbonate (800 mL). Wash twice with ethyl acetate. Add ethyl acetate (200 mL), and acidify the aqueous layer in its presence to pH=3 with concentrated hydrochloric acid. Wash the organic layer with water, dry (Na2SO4), and concentrate to afford the title compound as a clear oil (12.7 g): 1H NMR (CDCl3) δ 1.45 (s, 9H), 1.70 (s, 3H), 3.65 (m, 1H), 3.85 (m, 1H), 3.86-3.94 (m, 2H), 4.44 (m, 1H), 4.89 (s, 1H), 4.93 (s, 1H), 5.43 (d, 1H).

Workup

  1. temperatureCool in an ice bath
  2. washWash twice with ethyl acetate
  3. washWash the organic layer with water
  4. dry with materialdry (Na2SO4)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-c47f8bafd4db4ba99d6c4b13b515613d
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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