Diisopropylethylamine → 4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)butyric acid methyl ester

HRID 1097015Notes

Reaction equation

HRID 1097015 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][CH2:7][NH:8][CH3:9].[C:11]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]([O:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29](O)=[O:30])[CH2:23][CH2:22]1)=[O:19].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.O>[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][CH2:7][NH:8][CH2:9][C:29](=[O:30])[CH2:28][CH2:27][N:24]1[CH2:25][CH2:26][CH:21]([O:20][C:18](=[O:19])[NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218806073-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic AcidHCID 21932544Methyl 4-(methylamino)butanoate hydrochloride

Product 1

HCID 667817944-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)butyric acid methyl esterYield 127.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 4-methylaminobutyric acid methyl ester hydrochloride (546 mg, 3.26 mmol) and 3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic acid (1.20 g, 3.26 mmol) in DCM (15 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.36 g, 3.58 mmol) followed by N,N-diisopropylethylamine (1.42 mL, 8.15 mmol). LC-MS (Method 2-90) showed product was present (Rt 3.11 min; m/z 482.4 [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 (2.0 g, 100% yield) as a light yellow oil.

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-922e9b9c00164263b1b6c60b23fa91d5
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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