Water → HCID 67175826, compound

HRID 731024Notes

Reaction equation

HRID 731024 reaction equation
[H-].[Na+].N1C=[CH:6][N:5]=[N:4]1.Cl[CH2:9][C@:10]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29])([OH:21])[C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH3:12].O.[CH3:31][N:32](C=O)C>C(OCC)(=O)C>[Si:14]([O:13][C@@H:11]([CH3:12])[C@:10]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29])([OH:21])[CH2:9][N:5]1[CH:6]=[N:32][CH:31]=[N:4]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 67175909HCID 67175909, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 67175826HCID 67175826, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.22 g (5.4 mmol) of sodium hydride (60% content) in 3 mL of DMF was added 0.37 g (5.4 mmol) of triazole. Furthermore, a solution of 0.63 g (1.8 mmol) of (2R,3S)-1-chloro-2-(2,4-difluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol in 10 mL of DMF was added thereto. The resulting reaction mixture was stirred at room temperature for 2 hours and then at 50° C. for 12 hours. Next, 10 mL of water was added to stop the reaction, and extraction was performed with ethyl acetate (30 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The resulting product was purified by column on silica gel to obtain 0.18 g of the title compound (yield: 25%). 1H-NMR (400 MHz, CDCl3) δ: 0.22 (s, 6H), 0.97 (s, 12H), 4.42 (dq, 1H, J=5.9, 1.2 Hz), 4.54 (d, 1H, J=1.4 Hz), 4.81 (d, 1H, J=1.4 Hz), 6.67-6.78 (m, 2H), 7.32-7.38 (m, 1H), 7.71 (s, 1H), 7.96 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. waitat 50° C. for 12 hours
  3. customthe reaction, and extraction
  4. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  5. customto obtain a crude product
  6. customThe resulting product was purified by column on silica gel

Sources & evidence

ORD record
ord-7d1a3a565229417f80500341b27c66d5
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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