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

HRID 1055295Notes

Reaction equation

HRID 1055295 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([CH2:15][CH2:16][CH2:17][N:18]([CH3:45])[C:19]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([O:29][C:30](=[O:44])[NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:25][CH2:24]2)=[O:20])=[O:14])=[CH:8][CH:7]=1.Cl.O>C(#N)C>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([CH2:15][CH2:16][CH2:17][N:18]([CH3:45])[C:19]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([O:29][C:30](=[O:44])[NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:27][CH2:28]2)=[O:20])=[O:14])=[CH:8][CH:7]=1)=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 66772650Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)propyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

Product 1

HCID 86646959Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-Formylphenylcarbamoyl)-propyl]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)propyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (98 mg, 0.16 mmol) in acetonitrile (2 mL) was added aqueous hydrochloric acid (3 M, 1.07 mL). The resulting dark orange solution was stirred at room temperature. Water was added and the resulting mixture was extracted with DCM (2×). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification.

Workup

  1. extractionthe resulting mixture was extracted with DCM (2×)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29567a5d17a04064810559d904640f91
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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