Pyridine → HCID 68816131, compound

HRID 735568Notes

Reaction equation

HRID 735568 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[C:6]([CH:19]=1)[CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:25](Cl)Cl.Cl[C:29]([O:31]C1C=CC=CC=1)=[O:30].N1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH2:11]([O:10][C:9]([NH:8][CH2:7][C:6]1[CH:19]=[C:2]([N:1]([C:39]2[CH:25]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:29](=[O:30])[OH:31])[CH:3]=[CH:4][C:5]=1[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 15891Phenyl chloroformateHCID 57842737HCID 57842737, compound

Product 1

HCID 68816131HCID 68816131, compoundYield 62%

Procedure

To a solution of 28A (1 g, 3 mmol), DCM (10 mL) and pyridine (10 mL) at 0° C. was added phenyl chloroformate (0.38 mL, 3 mmol) dropwise over 30 min. The reaction was quenched with 1 N HCl (50 mL) and extracted with EtOAc (3×30 mL). The combined organics were washed with saturated NaHCO3, brine and dried (MgSO4). The organic layer was concentrated in vacuo and the residue purified by flash chromatography (0-100% EtoAc/Hexane) to afford 28B (877 mg, 62%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (t, 3 H) 5.06 (d, J=8.35 Hz, 4 H) 7.09-7.19 (m, 5 H) 7.31-7.36 (m, 5 H) 7.42-7.47 (m, 1 H) 7.70 (d, J=8.79 Hz, 1 H) 7.83 (d, J=8.35 Hz, 1 H).

Workup

  1. customThe reaction was quenched with 1 N HCl (50 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organics were washed with saturated NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue purified by flash chromatography (0-100% EtoAc/Hexane)

Sources & evidence

ORD record
ord-72ab626c7e6d4e4d9cd3c90bcbc6029a
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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