Hydrochloric Acid → HCID 66961172, compound

HRID 1362762Notes

Reaction equation

HRID 1362762 reaction equation
CCl.C[O:4][C:5](=[O:17])[C:6]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)([CH3:9])[CH2:7][OH:8].C(N(C(C)C)CC)(C)C.[CH3:27][O:28][CH2:29]Cl.Cl>C(OCC)(=O)C.C1COCC1>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]([CH3:9])([CH2:7][O:8][CH2:27][O:28][CH3:29])[C:5]([OH:4])=[O:17])=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6327Methyl ChlorideHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 66961629HCID 66961629, compound

Product 1

HCID 66961172HCID 66961172, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a methyl chloride (10 mL)-and-THF (5 mL) solution of 2-(4-fluorophenyl)-3-hydroxy-2-methylpropionic acid methyl ester (825 mg) synthesized according to the method described in Tetrahedron Letters, 1999, vol. 40, p. 5467, IPEA (2 mL) and chloromethyl methyl ether (0.74 mL) were added at 0° C. The reaction solution was agitated at 0° C. for 1 hour, and then at room temperature for 10 hours. 1N hydrochloric acid and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer obtained was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and then concentrated under reduced pressure. To a methanol (5 mL) solution of the obtained residue, 5N sodium hydroxide aqueous solution (4 mL) was added, and the reaction solution was agitated at room temperature for 10 hours. 5N hydrochloric acid (4 mL) and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer obtained was dried over magnesium sulfate and concentrated under reduced pressure to obtain 850 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. waitat room temperature for 10 hours
  2. customthe organic layer was partitioned
  3. customThe organic layer obtained
  4. washwas washed with saturated sodium bicarbonate water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo a methanol (5 mL) solution of the obtained residue, 5N sodium hydroxide aqueous solution (4 mL) was added
  8. stirringthe reaction solution was agitated at room temperature for 10 hours
  9. addition5N hydrochloric acid (4 mL) and ethyl acetate were added to the reaction solution
  10. customthe organic layer was partitioned
  11. customThe organic layer obtained
  12. dry with materialwas dried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c474d6e65dba4c0aac7041ff0fc39a09
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

Loading…