Hydrochloric Acid → Methyl 1-(4-methoxyphenylsulfonamido)cyclohexanecarboxylate

HRID 1642135Notes

Reaction equation

HRID 1642135 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(N(C(C)C)CC)(C)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>C(Cl)Cl.O>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH:12][C:6]2([C:4]([O:3][CH3:2])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 22907072Methyl 1-(4-methoxyphenylsulfonamido)cyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-Amino-cyclohexanecarboxylic acid methyl ester hydrochloride (32 g, 165 mmol) was suspended in DCM (1000 ml), and diisopropylethylamine (84.9 ml, 496 mmol) was added thereto. A solution of 4-methoxybenzenesulfonyl chloride (51.2 g, 248 mmol) dissolved in DCM (150 ml) was added dropwise at 0° C., and stirring was carried out overnight at room temperature. Aqueous 1 M HCl (150 ml) and water (50 ml) were added and the phases were separated. The organic phase was dried over sodium sulfate and concentrated to dryness. The product was purified by column chromatography on silica gel (DCM/methanol 99:1).

Workup

  1. additionwas added dropwise at 0° C.
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe product was purified by column chromatography on silica gel (DCM/methanol 99:1)

Sources & evidence

ORD record
ord-8933920d1afc457ea881534a8494f13b
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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