Sodium hydride → HCID 86726494, compound

HRID 1487660Notes

Reaction equation

HRID 1487660 reaction equation
CS(O[CH2:6][C@H:7]([NH:9][C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([O:20][CH3:21])[CH:12]=1)[CH3:8])(=O)=O.[H-].[Na+]>C1COCC1>[CH3:21][O:20][C:13]1[CH:12]=[C:11]([C:10]([N@@:9]2[CH2:6][CH:7]2[CH3:8])=[O:22])[CH:16]=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86726492HCID 86726492, compound

Product 1

HCID 86726494HCID 86726494, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-2-(3-methoxy-4-nitrobenzamido)propyl methanesulfonate (1 equiv) in THF (0.14 M) was added sodium hydride (4 equiv, 60% in mineral oil). The mixture was stirred at 60° C. for 5 h. The reaction was quenched with aqueous ammonium chloride, diluted with ethyl acetate (0.16 M), and then washed with water (0.27 M) and brine (0.27 M). The aqueous layer was extracted with ethyl acetate (0.16 M). The combined organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated. The crude compound was purified by silica gel chromatography (15% ethyl acetate in petroleum ether) to afford the desired compound (71% yield). MS (ESI) m/z 235.1 [M+H]+.

Workup

  1. customThe reaction was quenched with aqueous ammonium chloride
  2. additiondiluted with ethyl acetate (0.16 M)
  3. washwashed with water (0.27 M) and brine (0.27 M)
  4. extractionThe aqueous layer was extracted with ethyl acetate (0.16 M)
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe crude compound was purified by silica gel chromatography (15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9d5b7bfb4d134bc5800bcb96c499ba60
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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