Diisopropylethylamine → HCID 57657815, compound

HRID 391606Notes

Reaction equation

HRID 391606 reaction equation
[C:1]1([S@@:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])(=[NH:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=1)[C:33](O)=[O:34].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:27][C:28]1[CH:36]=[C:32]([C:33]([N:9]=[S@:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])=[O:34])[CH:31]=[N:30][CH:29]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 57657850HCID 57657850, compound

Product 1

HCID 57657815HCID 57657815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (S)-Methyl 5-(S-phenylsulfonimidoyl)pentanoate (475 mg, 1.86 mmol) in anhydrous DMF (6 mL) at room temperature under nitrogen atmosphere was added diisopropylethylamine (0.65 mL), 5-bromonicotinic acid (0.38 g), and (benzotriazol-1-yloxy)-tris(dimethylamino)-phosphonium hexafluorophosphate (0.81 g). The resulting reaction mixture was stirred for about 15 min at room temperature and then poured into saturated aqueous NaHCO3. The aqueous was extracted with EtOAc (1×), which was then washed with saturated aqueous NaHCO3 and brine (v:v 1:1, 2×), brine (1×), and dried with anhydrous sodium sulfate. The solution was decanted and concentrated with silica gel. A column chromatography (EtOAc-Hex 1:2) rendered the title compound as slightly yellow colored solid in amount of (616 mg, 75%).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe aqueous was extracted with EtOAc (1×), which
  3. washwas then washed with saturated aqueous NaHCO3 and brine (v:v 1:1, 2×), brine (1×)
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solution was decanted
  6. concentrationconcentrated with silica gel

Sources & evidence

ORD record
ord-2da21dd3b36c4574bd69dd5ac484d5f3
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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