Ethyl Acetate → HCID 86608208, compound

HRID 388357Notes

Reaction equation

HRID 388357 reaction equation
[Mg].[CH2:2]([O:9][C:10]([CH:12]1[NH:24][CH2:23][C:21]2=[C:22]3[C:17](=[C:18]([C:25]4[C:26](=[O:40])[NH:27][C:28](=[O:39])[C:29]=4[C:30]4[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[NH:32][CH:31]=4)[CH:19]=[CH:20]2)[CH:16]=[CH:15][N:14]3[CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)(=O)C>CO>[CH2:2]([O:9][C:10]([CH:12]1[NH:24][CH2:23][C:21]2=[C:22]3[C:17](=[C:18]([C@H:25]4[C@H:29]([C:30]5[C:38]6[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=6)[NH:32][CH:31]=5)[C:28](=[O:39])[NH:27][C:26]4=[O:40])[CH:19]=[CH:20]2)[CH:16]=[CH:15][N:14]3[CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5462224MagnesiumHCID 670171027-[4-(1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-3,4-dihydro-1H-[1,4]diazepino[6,7,1-hi]indole-2-carboxylic acid benzyl ester

Product 1

HCID 86608208HCID 86608208, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Magnesium turnings (195 mg, 8.0 mmol) were added to a solution of 7-[4-(1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-3,4-dihydro-1H-[1,4]diazepino[6,7,1-hi]indole-2-carboxylic acid benzyl ester (230 mg, 0.44 mmol) in anhydrous methanol (20 ml) and heated to reflux under an atmosphere of nitrogen for 1.5 hours. After cooling to room temperature the mixture was poured into ethyl acetate (200 ml) and washed with 1 M hydrochloric acid (100 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was then purified by silica gel chromatography using 50-60% ethyl acetate in hexanes to yield (±)-trans-7-[4-(1H-indol-3-yl)-2,5-dioxo-pyrrolidin-3-yl]-3,4-dihydro-1H-[1,4]diazepino[6,7,1-hi]indole-2-carboxylic acid benzyl ester as an off white solid (205 mg). 1H NMR (DMSO-d6) 400 MHz δ: 11.56 (s, 1H), 11.03 (d, 1H, J=2 Hz), 7.21-7.43 (m, 10H), 7.09 (t, 1H, J=7.2 Hz), 6.92-7.00 (m, 2H), 6.82-6.89 (m, 3H), 5.04 (s, 2H), 4.87 (d, 2H, J=7.6 Hz), 4.54 (dd, 2H, J=7.6 and 28.8 Hz), 4.30 (m, 2H), 3.92 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen for 1.5 hours
  3. washwashed with 1 M hydrochloric acid (100 ml)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-617910476fc34a4b8653fbd7821a4010
Source dataset
uspto-grants-2013_02
Patent number
US08377927B2

Reaction notes

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