Tetrahydrofuran → Methyl 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

HRID 494746Notes

Reaction equation

HRID 494746 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH2:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH3:13])=[C:8]([CH2:14][CH3:15])[CH:7]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([N:24]2[CH2:30][CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[NH:26][C:25]2=[O:35])[CH2:20][CH2:19]1.C1C[O:39][CH2:38]C1>C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:16][C:38]([N:18]1[CH2:19][CH2:20][CH:21]([N:24]2[CH2:30][CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[NH:26][C:25]2=[O:35])[CH2:22][CH2:23]1)=[O:39])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH3:13])=[C:8]([CH2:14][CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 22184541HCID 22184541, compound2×

Product 1

HCID 22184617Methyl 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

7.4 g (45 mmol) of CDT was added to a solution of 10.5 g (44.6 mmol) methyl-2-amino-3-(3,4-diethyl-phenyl)-propionate (Intermediate product 48) in 250 mL THF cooled to 0° C. and the resulting mixture was stirred for a further 30 minutes at this temperature. Then 10.9 g (44.6 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one was added, while the reaction solution was kept at this temperature for a further 20 minutes, before being refluxed for 30 minutes. The solvent was eliminated in vacuo, the residue was taken up in sat. sodium bicarbonate solution, exhaustively extracted with ether/EtOAc (1:1) and dried over magnesium sulphate. After removal of the drying agent and solvent the crude product was reacted without any further purification.

Workup

  1. waitwas kept at this temperature for a further 20 minutes
  2. temperaturebefore being refluxed for 30 minutes
  3. extractionexhaustively extracted with ether/EtOAc (1:1)
  4. dry with materialdried over magnesium sulphate
  5. customAfter removal of the drying agent and solvent the crude product
  6. customwas reacted without any further purification

Sources & evidence

ORD record
ord-b3af7de4559a4119bd19060e481be41c
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

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