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 1097045Notes

Reaction equation

HRID 1097045 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-67a1b2e117014ec092673eeec0709bd5
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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