HCID 178499276, compound → HCID 178499271, compound

HRID 1190000Notes

Reaction equation

HRID 1190000 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-49ef48bd0b3149259a275a6206572034
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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