Hydrochloric Acid → Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-Formylphenylcarbamoyl)-phenyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 1055336Notes

Reaction equation

HRID 1055336 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:16]=[C:17]([CH2:21][NH:22][C:23]([CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([O:33][C:34](=[O:48])[NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH2:29][CH2:28]3)=[O:24])[CH:18]=[CH:19][CH:20]=2)=[O:14])=[CH:8][CH:7]=1.Cl.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:16]=[C:17]([CH2:21][NH:22][C:23]([CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH:30]([O:33][C:34](=[O:48])[NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH2:31][CH2:32]3)=[O:24])[CH:18]=[CH:19][CH:20]=2)=[O:14])=[CH:8][CH:7]=1)=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66771841Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)phenyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

Product 1

HCID 86646970Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-Formylphenylcarbamoyl)-phenyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of biphenyl-2-ylcarbamic acid 1-(2-{[3-(4-(1,3-dioxolan-2-yl)phenylcarbamoyl)phenyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (345 mg containing some solvent residue, ca. 0.500 mmol) in acetonitrile (2.00 mL) at room temperature was added aqueous hydrochloric acid (1 N, 2.00 mL). The reaction mixture was stirred at room temperature for 3 h. LC-MS (Method 10-90) showed product was present (Rt 3.45 min; m/z 605.0 [M+H]+. Saturated aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the next reaction without further purification.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e79759050694c4e8457e0c456424777
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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