Hydrochloric Acid → HCID 178501241, compound

HRID 2223374

Reaction equation

HRID 2223374 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[C:21]([O:23][CH2:24][CH2:25][Cl:26])=[O:22].Cl>C(Cl)(Cl)Cl>[Cl:26][CH2:25][CH2:24][O:23][C:21]([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:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 123052-Chloroethyl chloroformateHCID 178501210HCID 178501210, compound

Product 1

HCID 178501241HCID 178501241, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (5.00 g) obtained in Reference Example 2(1) is dissolved in chloroform (60 ml), and thereto is added triethylamine (11 ml) under ice-cooling, followed by dropwise addition of a solution of 2-chloroethyl chloroformate (3.3 ml) in chloroform (10 ml). After stirring at room temperature for 2.5 hours, to the reaction solution is added 5% hydrochloric acid and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate, and then evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in chloroform/diisopropyl ether. The precipitates are collected by filtration and dried to give methyl trans-4-{[(2-chloroethoxy)carbonyl]amino}cyclohexanecarboxylate (5.11 g). APCI-MS M/Z:264/266[M+H]+

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. filtrationThe precipitates are collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-44edf5fd6f154e9993b019471330ef31
Source dataset
uspto-grants-2008_05
Patent number
US07375119B2

Linked notes

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