Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester → Biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-formylphenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester

HRID 2412271Notes

Reaction equation

HRID 2412271 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][CH2:18][N:19]([CH3:46])[C:20]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([O:30][C:31](=[O:45])[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:26][CH2:25]2)=[O:21])=[O:14])=[CH:8][CH:7]=1>Cl.C(#N)C>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH3:46])[C:20]([CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([O:30][C:31](=[O:45])[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:28][CH2:29]2)=[O:21])=[O:14])=[CH:8][CH:7]=1)=[O:1]

Participants

4

Reactant 1

HCID 66771476Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

Product 1

HCID 86646966Biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-formylphenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl esterYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-(1,3-dioxolan-2-yl)phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (3.04 g, 4.84 mmol) in aqueous hydrochloric acid (1 M, 10 mL) and acetonitrile (10 mL) was heated at 50° C. for 2 h. The reaction mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution and DCM were added to the residue. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (2.83 g, 100% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution and DCM
  2. additionwere added to the residue
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f635bc17cb604fbebb77548f1d84d437
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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