HCID 86753586, compound → HCID 67699881, compound

HRID 343193Notes

Reaction equation

HRID 343193 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([N:12]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:13](=[O:38])[CH2:14][N:15]1[C:21](=[O:22])[C:20]([CH3:26])([CH2:23][CH:24]=[O:25])[C:19](=[O:27])[N:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]2[CH:34]=[CH:35][CH:36]=[CH:37][C:16]1=2)([CH3:11])[CH3:10].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C1COCC1.Cl>[CH:9]([N:12]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:13](=[O:38])[CH2:14][N:15]1[C:21](=[O:22])[C:20]([CH3:26])([CH2:23][C:24]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:25])[C:19](=[O:27])[N:18]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:17]2[CH:34]=[CH:35][CH:36]=[CH:37][C:16]1=2)([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 86753586HCID 86753586, compoundHCID 178418255HCID 178418255, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67699881HCID 67699881, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.23 mL of 1.0M phenylmagnesium bromide in THF is added to a solution of 0.10 g (0.21 mmol) of N-Isopropyl-2-[3-methyl-2,4-dioxo-3-(2-oxoethyl)-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide, prepared as in Intermediate 9, in 2 mL of THF at 0° C. After stirring at room temperature for 60 min the reaction is diluted with 10 mL of 1N HCl and extracted with EtOAc (×3). The organic extract is washed with sat. NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to a colorless oil. The crude product is dissolved in 2 mL of CH2Cl2 and 0.092 g (0.42 mmol) of PCC added. After stirring at RT for 90 min, the reaction mixture is passed through a short plug of silica gel and concentrated in vacuo to a dark orange oil. Purification by silica gel flash chromatography (30% ethyl acetate/petroleum ether) gave 97 mg of the title compound as a white powder; 1H NMR (CDCl3 300 MHz) δ8.04 (d, 2H, J=7), 7.6-7.2 (m, 15H), 7.14 (t, 1H, J=7), 7.00 (d, 1H, J=7), 5.03 (m, 1H), 4.2 (m, 2H), 3.98 (dd, 1H, J=8,18), 3.61 (dd, 1H, J=5,18), 1.09 (dd, 1H, J=2,7); low resolution MS (FAB) m/e 546 (MH+).

Workup

  1. extractionextracted with EtOAc (×3)
  2. extractionThe organic extract
  3. washis washed with sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo to a colorless oil
  6. dissolutionThe crude product is dissolved in 2 mL of CH2Cl2
  7. stirringAfter stirring at RT for 90 min
  8. concentrationconcentrated in vacuo to a dark orange oil
  9. customPurification by silica gel flash chromatography (30% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-32ca868f5e5145f9a7e063ba97cd01b6
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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