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

HRID 1097018Notes

Reaction equation

HRID 1097018 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-77a6ad19ee884078bd8ea83ecf722df6
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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