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 644300Notes

Reaction equation

HRID 644300 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([CH2:16][CH3:17])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[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>>[CH2:16]([C:10]1[CH:9]=[C:8]([CH2:7][CH:2]([NH:1][C:38]([N:18]2[CH2:19][CH2:20][CH:21]([N:24]3[CH2:30][CH2:29][C:28]4[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=4[NH:26][C:25]3=[O:35])[CH2:22][CH2:23]2)=[O:39])[C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:12][C:11]=1[CH2:14][CH3:15])[CH3:17]

Participants

4

Reactant 3

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

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

Conditions

Temperature
0 °C

Procedure

7.4 g (45 mmol) of CDT were added to a solution of 10.5 g (44.6 mmol) of methyl 2-amino-3-(3,4-diethyl-phenyl)-propionate in 250 mL of THF cooled to 0° C. and stirred for a further 30 min at this temperature. Then 10.9 g (44.6 mmol) of 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one was added and the reaction solution was kept for a further 20 min at this temperature before being refluxed for 30 min. The solvent was removed in vacuo, the residue was taken up in saturated NaHCO3 solution, exhaustively extracted with diethyl ether/EtOAc (1:1) and dried over MgSO4. After elimination of the desiccant and solvent the crude product was reacted without any further purification.

Workup

  1. waitthe reaction solution was kept for a further 20 min at this temperature
  2. temperaturebefore being refluxed for 30 min
  3. customThe solvent was removed in vacuo
  4. extractionexhaustively extracted with diethyl ether/EtOAc (1:1)
  5. dry with materialdried over MgSO4
  6. customAfter elimination of the desiccant and solvent the crude product was reacted without any further purification

Sources & evidence

ORD record
ord-ea71b382842142928ed1b044eb0d82e6
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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