HCID 178499276, compound → HCID 178499271, compound

HRID 1694448Notes

Reaction equation

HRID 1694448 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:24]2[CH:28]=[C:27]([C:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=3)[S:26][C:25]=2[C:35]([O:37][CH3:38])=[O:36])[C:15]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH3:23])[CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH3:38][O:37][C:35]([C:25]1[S:26][C:27]([C:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=2)=[CH:28][C:24]=1[N:14]([C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH3:23])[CH2:19][CH2:18]1)=[O:16])[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:36]

Participants

4

Reactant 1

HCID 178499276HCID 178499276, compound

Product 1

HCID 178499271HCID 178499271, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[(5-cyclohex-1-enyl-2-methoxycarbonyl-thiophen-3-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (2.3 g, 4.22 mmol) in dichloromethane (15 mL) and trifluoroacetic acid (15 mL) was stirred at room temperature under N2 atmosphere for 4 h. Solvents were removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using methanol, chloroform and triethyl amine (10:89:1) as eluent to obtain 5-cyclohex-1-enyl-3-[(trans-4-methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-thiophene-2-carboxylic acid methyl ester (1.5 g, 80%) as a solid.

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1821152bc8a4af59338dfc94b9bd2ca
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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