Phosphorus oxychloride → HCID 11547193, compound

HRID 1174532Notes

Reaction equation

HRID 1174532 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@@H:12]2[C@H:17]([NH:18][C:19](=O)[C:20]3[CH:34]=[CH:33][C:23]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=3)[CH2:16][CH2:15][O:14][CH2:13]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].O=P(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][C:9]=1[O:10][CH3:11])[C:19]([C:20]1[CH:34]=[CH:33][C:23]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=1)=[N:18][C@H:17]1[C@@H:12]2[CH2:13][O:14][CH2:15][CH2:16]1)[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59006937HCID 59006937, compound

Product 1

HCID 11547193HCID 11547193, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 mmol of N-[(3R,4R)-3-(3-Ethoxy-4-methoxy-phenyl)-tetrahydro-pyran-4-yl]-N′,N′-diisopropyl-terephthalamide are heated to boiling under reflux for 4 h in 25 ml of acetonitrile and 15 mmol of phosphorus oxytrichloride. After distilling off the excess of phosphorus oxytrichloride and about 20 ml of acetonitrile, the residue is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution. The organic phase is washed with water, dried over sodium sulfate and concentrated. The solid residue is purified by column chromatography on SiO2 (di-isopropylether/methanol/triethyl amine 18/1/1 vol/vol/vol), the main product fraction is separated and concentrated yielding the title compound as grayish solid foam. M.p. 98-102° C. (unsharp, enamel-like shrinking starting at about 88° C.)

Workup

  1. distillationAfter distilling off the excess of phosphorus oxytrichloride and about 20 ml of acetonitrile
  2. customthe residue is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe solid residue is purified by column chromatography on SiO2 (di-isopropylether/methanol/triethyl amine 18/1/1 vol/vol/vol)
  7. customthe main product fraction is separated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-862279ed8ce645ac83e2a1b230b50ecb
Source dataset
uspto-grants-2010_11
Patent number
US07838521B2

Reaction notes

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