Pyridine → HCID 70236820, compound

HRID 651548Notes

Reaction equation

HRID 651548 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:45])[O:16][C@@H:17]2[C@@H:29]3[C:30](=[O:33])[O:31][CH2:32][C@H:28]3[C@H:27]([C:34]3[CH:39]=[C:38]([O:40][CH3:41])[C:37]([OH:42])=[C:36]([O:43][CH3:44])[CH:35]=3)[C:26]3[C:18]2=[CH:19][C:20]2[O:24][CH2:23][O:22][C:21]=2[CH:25]=3)=[CH:10][CH:9]=1.Cl[C:47]([O:49][C:50]1[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][CH:51]=1)=[O:48].C([O-])(O)=O.[Na+]>ClCCl>[C:47](=[O:48])([O:49][C:50]1[CH:51]=[CH:52][C:53]([N+:56]([O-:58])=[O:57])=[CH:54][CH:55]=1)[O:42][C:37]1[C:36]([O:43][CH3:44])=[CH:35][C:34]([C@H:27]2[C@@H:28]3[CH2:32][O:31][C:30](=[O:33])[C@H:29]3[C@@H:17]([O:16][C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=3)=[O:45])[C:18]3[C:26]2=[CH:25][C:21]2[O:22][CH2:23][O:24][C:20]=2[CH:19]=3)=[CH:39][C:38]=1[O:40][CH3:41]

Participants

6

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 69843583HCID 69843583, compound

Product 1

HCID 70236820HCID 70236820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.07 mmol of pyridine and then, dropwise, a solution of 0.59 mmol of the compound of Example 4 in 5 ml of dichloromethane, are added, under argon, to a solution of 0.83 mmol of para-nitrophenyl chloroformate in 20 ml of anhydrous dichloromethane. After stirring for 1 hour, the reaction mixture is hydrolysed by the addition of a saturated aqueous NaHCO3 solution, and then the extracted organic phases are washed, neutralised, dried, filtered and concentrated under reduced pressure. Chromatography on silica gel (cyclohexane/ethyl acetate: 3/1) enables the expected product to be isolated.

Workup

  1. washthe extracted organic phases are washed
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto be isolated

Sources & evidence

ORD record
ord-539848b7fe26451fbf7ee65f05814d28
Source dataset
uspto-grants-2001_08
Patent number
US06281198B1

Reaction notes

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