Sodium hydride → (R)-Methyl 2-(((2-((tert-butoxycarbonyl)amino)pent-4-en-1-yl)oxy)methyl)benzoate

HRID 1429380Notes

Reaction equation

HRID 1429380 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH2:11][CH:12]=[CH2:13])[CH2:9][O:10][CH2:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 11106388Carbamic acid, [(1R)-1-(hydroxymethyl)-3-butenyl]-, 1,1-dimethylethyl ester

Product 1

HCID 68233281(R)-Methyl 2-(((2-((tert-butoxycarbonyl)amino)pent-4-en-1-yl)oxy)methyl)benzoateYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 18g (6.2 g, 30.8 mmol) and compound 18c (8.5 g, 36.9 mmol) in THF (30 mL) was cooled in an ice bath under argon. To this mixture was added NaH (2.5 g, 61.6 mmol, 60% wt in oil) portionwise. The ice bath was removed and the reaction mixture was allowed to stir at rt for 2 h and then quenched with MeOH (10 mL). The mixture was concentrated under reduced pressure and the residue was purified by CC to give the desired compound 18h (4.2 g, 39% yield) as a yellow oil. LCMS (m/z): 350.2 (MH+).

Workup

  1. customThe ice bath was removed
  2. customquenched with MeOH (10 mL)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by CC

Sources & evidence

ORD record
ord-e735fed5baa0455bb0e59d5f787a7820
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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