(E)-3-(1-ethyl 3,3,5-trimethyl 2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) acrylic acid ethyl ester → 3-(1-ethyl 3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) propionic acid ethyl ester

HRID 68946Notes

Reaction equation

HRID 68946 reaction equation
[CH2:1]([O:3][C:4](=[O:25])/[CH:5]=[CH:6]/[C:7]1[CH:24]=[CH:23][C:10]2[N:11]([CH2:21][CH3:22])[C:12](=[O:20])[C:13]([CH3:19])([CH3:18])[C:14](=[O:17])[N:15]([CH3:16])[C:9]=2[CH:8]=1)[CH3:2]>[Pd].CO>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1[CH:24]=[CH:23][C:10]2[N:11]([CH2:21][CH3:22])[C:12](=[O:20])[C:13]([CH3:19])([CH3:18])[C:14](=[O:17])[N:15]([CH3:16])[C:9]=2[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 66960494(E)-3-(1-ethyl 3,3,5-trimethyl 2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) acrylic acid ethyl ester

Product 1

HCID 669611763-(1-ethyl 3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) propionic acid ethyl esterYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.1 g) was added to a methanol solution (10 ml) of (E)-3-(1-ethyl 3,3,5-trimethyl 2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) acrylic acid ethyl ester (0.36 g). The mixture was subjected to catalytic reduction at room temperature and under normal pressure. The catalyst was removed by celite filtration, followed by concentration under reduced pressure to give the title compound (0.29 g) as a brown solid.

Workup

  1. customwas subjected to catalytic reduction at room temperature and under normal pressure
  2. customThe catalyst was removed by celite filtration
  3. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-2ffeefea3ad44029bebffcb9c1801faf
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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