Nitromethane → HCID 90014160, compound

HRID 1520788Notes

Reaction equation

HRID 1520788 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:34])/[CH:20]=[C:21](/[C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=3)\[C:22]([F:25])([F:24])[F:23])=[CH:15][CH:14]=2)([F:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:35]([CH3:38])([O-:37])=[O:36].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:34])[CH2:20][C:21]([C:26]3[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=3)([CH2:38][N+:35]([O-:37])=[O:36])[C:22]([F:23])([F:25])[F:24])=[CH:15][CH:14]=2)([F:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 71680325HCID 71680325, compound

Product 1

HCID 90014160HCID 90014160, compoundYield 81.34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the stirred solution of 3-{4-[(Z)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-phenyl}-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester (1.2 g, 2.315 mmol, 1 eq.) in acetonitrile (10 mL) was added nitro methane (1.24 mL, 23.152 mmol, 10 eq) and DBU (0.33 mL, 2.246 mmol, 0.97 eq) at room temperature. The resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, the reaction mixture was quenched with water (25 mL) and extracted with ethyl acetate (2×25 mL). Combined organic layers were washed with brine (60 mL), dried over sodium sulphate and concentrated to get crude compound semi solid (1.37 g, crude). Crude compound was purified by column chromatography on silica gel using 230-400 mesh. Desired compound was eluted in 10% ethyl acetate in n-hexane to give product as light yellow sticky liquid (1.09 g, 81.34%). LC-MS (m/z): 576.8 (M−H).

Workup

  1. customThe resulting reaction mixture
  2. customAfter complete consumption of starting material
  3. customthe reaction mixture was quenched with water (25 mL)
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washCombined organic layers were washed with brine (60 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customto get crude compound semi solid (1.37 g, crude)
  9. customCrude compound was purified by column chromatography on silica gel using 230-400 mesh
  10. washDesired compound was eluted in 10% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-d6456a2712154e96b20943b660d5af20
Source dataset
uspto-grants-2015_07
Patent number
US09073912B2

Reaction notes

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