Acetic Acid Mixture with Hydrobromic Acid → HCID 86648761, compound

HRID 43816Notes

Reaction equation

HRID 43816 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:22][C:21]([CH3:23])=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:19]=2)[CH2:14][C@H:13]1[O:28][CH3:29])=O)C1C=CC=CC=1.Br.C(O)(=O)C>C(O)(=O)C.C(OCC)(=O)C>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:22][C:21]([CH3:23])=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:19]=2)[CH2:14][C@H:13]1[O:28][CH3:29]

Participants

5

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86648760HCID 86648760, compound

Product 1

HCID 86648761HCID 86648761, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl cis(±)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylthiophene-3-carboxylate obtained in Example (188c) (50 mg) was dissolved in acetic acid (1 mL). A hydrobromic acid-acetic acid solution (1 ml) was added, and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0, 10%) to obtain 20 mg of the title compound as a glassy solid (59%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0, 10%)

Sources & evidence

ORD record
ord-156ed93175834bcead88774dca9f4d4e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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