Water → Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)propyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 2412244Notes

Reaction equation

HRID 2412244 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19](CNCCCC(O)=O)=[O:20])[CH2:13][CH2:12]1)=[O:9].[O:35]1[CH2:39][CH2:38][O:37][CH:36]1[C:40]1[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1[C:62]2[N:63]=[CH:64][CH:65]=[CH:66][C:61]=2N=N1.C(N(CC)C(C)C)(C)C.[OH2:80]>C(Cl)Cl>[O:35]1[CH2:39][CH2:38][O:37][CH:36]1[C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:61]([CH2:66][CH2:65][CH2:64][N:63]([CH3:62])[C:19]([CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([O:10][C:8](=[O:9])[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:12][CH2:13]2)=[O:20])=[O:80])=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 962WaterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 111266244-(1,3-Dioxolan-2-yl)anilineHCID 667816914-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)butyric Acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-({3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)butyric acid (75 mg, 0.16 mmol) and 4-(1,3-dioxolan-2-yl)phenylamine (26 mg, 0.16 mmol) in DCM (3 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (73.2 mg, 0.192 mmol) followed by N,N-diisopropylethylamine (55.9 μL, 0.321 mmol). The reaction mixture was stirred at room temperature for about 48 h. LC-MS (Method 2-90) showed product was present (Rt 3.87 min; m/z 615.4 [M+H]+). Water and DCM were added and the layers were separated. The organic layer was washed with water (2×) and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as a yellow oil, which was used without further purification. In subsequent experiments, this compound was also isolated as a filterable solid.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water (2×) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2999c4af31740259276b5790c25199b
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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