Pyridine → HCID 178496221, compound

HRID 53463Notes

Reaction equation

HRID 53463 reaction equation
[C:1]([O:5][C:6](/[C:8](/[CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:9]/[C:10]1([C:15](O)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.S(Cl)(Cl)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:45][C@@H:46]1[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[O:53])[CH2:48][CH2:47]1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O.O>[C:1]([O:5][C:6](/[C:8](/[CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:9]/[C:10]1([C:15]([NH:45][C@@H:46]2[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[O:53])[CH2:48][CH2:47]2)=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11069968(E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acidHCID 178427656HCID 178427656, compound

Product 1

HCID 178496221HCID 178496221, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid (1.0 g, 3.04 mmol) in ethyl acetate (10.6 mL) under a nitrogen atmosphere at room temperature was added dimethylformamide (1 drop), pyridine (0.49 mL, 6.08 mmol) and thionyl chloride (0.28 mL, 3.95 mmol) and the mixture stirred at room temperature for 40 minutes. Benzyl cis-4-amino-1-cyclohexanecarboxylate p-toluenesulphonate (1.29 g, 3.19 mmol) was added at room temperature followed by triethylamine (1.27 mL, 9.12 mmol) and the mixture stirred at room temperature for 3 hours. The reaction mixture was diluted with distilled water (50 mL) and ethyl acetate (50 mL) and the layers separated. The ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (1.552 g). The crude product was purified by chromatography on silica by elution with hexane/ethyl acetate (1:1) to give, after combination and evaporation of appropriate fractions, the title compound as an oil (1.07 g, 65%).

Workup

  1. stirringthe mixture stirred at room temperature for 3 hours
  2. customthe layers separated
  3. washThe ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd5674891c5140d7b096a8298f271e93
Source dataset
uspto-grants-1997_04
Patent number
US05618970

Reaction notes

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