Pyridine → HCID 67374254, compound

HRID 1677056Notes

Reaction equation

HRID 1677056 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].ClCCl.[F:10][C:11]1[CH:12]=[C:13]([C@H:19]2[NH:24][C@H:23]([CH:25]([OH:27])[CH3:26])[CH2:22][O:21][CH2:20]2)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].N1C=CC=CC=1>O>[CH3:26][CH:25]1[C@H:23]2[CH2:22][O:21][CH2:20][C@@H:19]([C:13]3[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=3)[N:24]2[C:2](=[O:3])[C:1](=[O:5])[O:27]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 67374557HCID 67374557, compound

Product 1

HCID 67374254HCID 67374254, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, oxalyl chloride (0.27 mL) was added dropwise into a dichloromethane (5 mL) solution containing 1-[(3S,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanol (269 mg) and pyridine (5 mL). Stirring was continued for 30 minutes at the same temperature and for 1 hour at room temperature. Water was added, and the organic layer was partitioned, and the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the resultant was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate), and the title compound (136 mg) was obtained. The physical property values are as follows.

Workup

  1. temperatureUnder ice-cooling
  2. customthe organic layer was partitioned
  3. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under a vacuum
  5. customthe resultant was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate)

Sources & evidence

ORD record
ord-67debe9f2b4f4e35bff7c36e03d49cd8
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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