Sodium hydride → HCID 44193422, compound

HRID 1850002Notes

Reaction equation

HRID 1850002 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[H-].[Na+].Br[C:12]([CH3:26])([CH3:25])[C:13]([NH:15][C:16]1[O:20][N:19]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:17]=1)=[O:14]>C1COCC1>[C:21]([C:18]1[CH:17]=[C:16]([NH:15][C:13](=[O:14])[C:12]([CH3:25])([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH3:26])[O:20][N:19]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 59703982HCID 59703982, compound

Product 1

HCID 44193422HCID 44193422, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (tetrahydro-pyran-4-yl)-methanol (4 mL) at room temperature is added NaH (55 mg of a 60% dispersion in oil, 1.4 mmol). The reaction is warmed to 50° C. and stirred for 30 min. After this time, 2-bromo-N-(3-tert-butyl-isoxazol-5-yl)-2-methyl-propionamide (0.20 g, 0.69 mmol) is added and THF (2 mL) is introduced. The reaction is stirred at 60° C. for 5 h before it is quenched by the addition of methanol. The solvent is removed under reduced pressure and the crude residue that remains is purified by preparative HPLC to give the title compound (38 mg, 17%). m/z 289 [M+H+].

Workup

  1. stirringThe reaction is stirred at 60° C. for 5 h before it
  2. customis quenched by the addition of methanol
  3. customThe solvent is removed under reduced pressure
  4. customthe crude residue that remains is purified by preparative HPLC

Sources & evidence

ORD record
ord-305d15bb876947608d424d4fb7abde7e
Source dataset
uspto-grants-2015_02
Patent number
US08957063B2

Reaction notes

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