Acetonitrile → HCID 86600096, compound

HRID 457709Notes

Reaction equation

HRID 457709 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C@@H:13]([N:15]([CH3:33])[C:16]([N:18]2[CH2:23][CH2:22][C:21](=O)[CH2:20][C@@H:19]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(O[BH-](O[C:46](=[O:48])[CH3:47])OC(=O)C)(=O)C.[Na+].[C:50](#[N:52])[CH3:51]>C(=O)([O-])O.[Na+]>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@@H:13]([N:15]([CH3:33])[C:16]([N:18]2[CH2:23][CH2:22][C@H:21]([N:52]3[CH2:50][CH2:51][N:15]4[CH2:13][CH2:5][CH2:4][C@H:47]4[C:46]3=[O:48])[CH2:20][C@@H:19]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])=[O:17])[CH3:14])[CH:4]=[C:3]([C:2]([F:34])([F:1])[F:35])[CH:8]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 57939525HCID 57939525, compound

Product 1

HCID 86600096HCID 86600096, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Intermediate 13a (250 mg) was added to a solution of intermediate 5b (449 mg) in anhydrous acetonitrile (9 mL) under a Nitrogen atmosphere. The solution was stirred at r.t. for 1 hour, then sodium triacetoxyborohydride (282 mg) was added. The mixture was stirred at 23° C. for 16 hours. The solution was diluted with a 5% sodium hydrogen carbonate solution (10 mL) and extracted with AcOEt (3×30 mL). The combined organic extracts were washed with brine (10 mL), dried and concentrated in vacuo to a residue which was purified by flash chromatography (AcOEt/MeOH 8:2) to give three fractions:

Workup

  1. stirringThe mixture was stirred at 23° C. for 16 hours
  2. extractionextracted with AcOEt (3×30 mL)
  3. washThe combined organic extracts were washed with brine (10 mL)
  4. customdried
  5. concentrationconcentrated in vacuo to a residue which
  6. customwas purified by flash chromatography (AcOEt/MeOH 8:2)
  7. customto give three fractions

Sources & evidence

ORD record
ord-4279cb46102c43eababd608cc29330af
Source dataset
uspto-grants-2007_03
Patent number
US07189713B2

Reaction notes

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