Thionyl Chloride → HCID 69345641, compound

HRID 1767101Notes

Reaction equation

HRID 1767101 reaction equation
[OH:1][CH:2]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]=1[F:34])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH:6]1[CH2:18][C:19]([OH:21])=[O:20].S(Cl)([Cl:37])=O>CO>[ClH:37].[ClH:37].[OH:1][CH:2]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]=1[F:34])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH:6]1[CH2:18][C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69345714HCID 69345714, compound

Product 1

HCID 69345641HCID 69345641, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 940 mg of (3RS,4RS) and (3SR,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid in 20 cm3 of methanol is cooled to a temperature in the region of −25° C., with stirring and under an inert atmosphere. 0.43 cm3 of thionyl chloride is added to this solution over 5 minutes. The mixture is brought back to a temperature in the region of 20° C., while the stirring is continued for a further 1 hour 30 minutes. The reaction mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and 30 cm3 of methanol are then added. This series of operations is repeated 3 times. 920 mg of methyl (3RS,4RS) and (3SR,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-3-acetate dihydrochloride, in the form of a yellow foam, are obtained.

Workup

  1. customis brought back to a temperature in the region of 20° C., while the stirring
  2. concentrationThe reaction mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and 30 cm3 of methanol
  3. additionare then added

Sources & evidence

ORD record
ord-7c4ad99ae869456d8d3d6a42b21eb777
Source dataset
uspto-grants-2007_06
Patent number
US07232834B2

Reaction notes

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