Hydrochloric Acid → HCID 178501253, compound

HRID 16700

Reaction equation

HRID 16700 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].Cl>C(Cl)(Cl)Cl>[Cl:20][CH2:21][CH2:22][CH2:23][S:24]([NH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 178501210HCID 178501210, compound

Product 1

HCID 178501253HCID 178501253, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (4.08 g) obtained in Reference Example 2(1) is suspended in chloroform (50 ml), and thereto is added triethylamine (8.8 ml) under ice-cooling. Subsequently, a solution of 3-chloropropanesulfonyl chloride (3.35 ml) in chloroform (20 ml) is added dropwise over 20 minutes under the same temperature. After stirring for 2 hours at room temperature, 5% hydrochloric acid is added to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diisopropylamine, and filtered to collect precipitates to give methyl trans-4-{[(3-chloropropyl)sulfonyl]amino}cyclohexanecarboxylate (6.14 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. filtrationfiltered
  8. customto collect
  9. customprecipitates

Sources & evidence

ORD record
ord-f13ca10a3f374ab6b0ddea3ebea60e36
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Linked notes

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