Hydrochloric Acid → HCID 69516592, compound

HRID 971161Notes

Reaction equation

HRID 971161 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[NH2:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]1[NH2:24].Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:15])[NH:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]3[NH2:24])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3429171,2-Diaminocyclohexane, cis-HCID 59020005HCID 59020005, compound

Product 1

HCID 69516592HCID 69516592, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A. 1-(4-Chlorocarbonyl-phenyl)-cyclopropanecarboxylic acid methyl ester (0.66 g, 2.77 mmol) was stirred in CH2Cl2 (10 mL) at rt under N2. 1,2-Cis-diamino-cyclohexane (0.66 mL, 2.0 eq) was added as one portion. The mixture was stirred for 10 min. Diluted HCl was added. The mixture was extracted with EtOAc (2×). The aqueous layer was basified with conc. NaOH, extracted with EtOAc (2×). The organic layers were washed with H2O and brine, dried over MgSO4, filtered, and concentrated to afford 1-[4-(2-amino-cyclohexylcarbamoyl)-phenyl]-cyclopropanecarboxylic acid methyl ester (0.35 g, yield: 39.8%). LC/MS (ESI+) 317.4 (M+H).

Workup

  1. extractionThe mixture was extracted with EtOAc (2×)
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed557d63c4d34b61a9106d58ab3d7280
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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