Sodium hydride → HCID 178434054, compound

HRID 1914670Notes

Reaction equation

HRID 1914670 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([CH3:8])[NH:4][N:3]=1.[H-].[Na+].[C:11]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25]OS(C(F)(F)F)(=O)=O)[CH2:21][CH2:20]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(#N)C.O>[C:11]([O:15][C:16](=[O:17])[NH:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([CH2:25][N:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[C:5]([CH3:8])=[N:4]2)[CH2:23][CH2:24]1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1385283,4,5-TrimethylpyrazoleHCID 178453974HCID 178453974, compound

Product 1

HCID 178434054HCID 178434054, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 3,4,5-trimethyl-1H-pyrazole (84 mg, 0.761 mmol) in dry acetonitrile (4 mL) at room temp is added sodium hydride (33 mg of a 60% dispersion on mineral oil, 0.83 mmol). The mixture is stirred at room temp for 10 minutes and then treated with a solution of trans-trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl ester (step 1) (250 mg, 0.692 mmol) in dry acetonitrile (3 mL). The reaction mixture is stirred at room temp for 17 hours. The mixture is diluted with water (20 mL) and extracted with EtOAc (3×10 mL). The EtOAc extracts are combined, washed with brine (20 mL), dried (MgSO4), filtered and evaporated to give the title compound as a colourless oil. This is used in the next step without further purification; MS m/z 322.4 [M+H]+.

Workup

  1. stirringThe reaction mixture is stirred at room temp for 17 hours
  2. extractionextracted with EtOAc (3×10 mL)
  3. washwashed with brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-eded235ceb684a95a07c3396330eaf7c
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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