Acetonitrile → HCID 56593955, compound

HRID 1174163Notes

Reaction equation

HRID 1174163 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11](#[N:13])[CH3:12].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C@H:29]([N:40]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:30](OCC2C=CC=CC=2)=[O:31])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH4+].[Cl-]>C1COCC1.O>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C@H:29]([N:40]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:30](=[O:31])[CH2:12][C:11]#[N:13])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 15248594HCID 15248594, compound

Product 1

HCID 56593955HCID 56593955, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

A solution of sodium bis(trimethylsilyl) amide (1 M in THF, 330 mL) at −45° C., was treated dropwise with acetonitrile (18.8 mL, 360 mmol) and the mixture was stirred for 15 minutes at −45° C. and then cooled to −78 ° C., treated dropwise with a solution of the product from Example 23A (53.5 g, 110 mmol) in THF (150 mL), warmed to −45° C., stirred for 1 hour, treated with solid NH4Cl (40 g), warmed to 5° C., treated with water, warmed to 25° C. and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. Precipitation from ethanol gave the product (19.0 g, 36% yield).

Workup

  1. temperaturecooled to −78 ° C.
  2. temperaturewarmed to −45° C.
  3. stirringstirred for 1 hour
  4. temperaturewarmed to 5° C.
  5. temperaturewarmed to 25° C.
  6. custompartitioned between ethyl acetate and water
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPrecipitation from ethanol

Sources & evidence

ORD record
ord-cdfc473bfacc4b729747ff49ab605c99
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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