Sodium periodate → N-Isopropyl-N-[4-methoxyphenyl]-2-[3-methyl-2,4-dioxo-3-(2-oxo-ethyl)-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]acetamide

HRID 343187Notes

Reaction equation

HRID 343187 reaction equation
[CH2:1]([C:4]1([CH3:38])[C:10](=[O:11])[N:9]([CH2:12][C:13]([N:15]([CH:24]([CH3:26])[CH3:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:14])[C:8]2[CH:27]=[CH:28][CH:29]=[CH:30][C:7]=2[N:6]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[C:5]1=[O:37])[CH:2]=C.I([O-])(=O)(=O)=[O:40].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O.O.CCOC(C)=O>[CH:24]([N:15]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[C:13](=[O:14])[CH2:12][N:9]1[C:10](=[O:11])[C:4]([CH3:38])([CH2:1][CH:2]=[O:40])[C:5](=[O:37])[N:6]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[C:7]2[CH:30]=[CH:29][CH:28]=[CH:27][C:8]1=2)([CH3:26])[CH3:25]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 676972302-(3-Allyl-3-methyl-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-[4-methoxyphenyl]acetamide

Product 1

HCID 86753596N-Isopropyl-N-[4-methoxyphenyl]-2-[3-methyl-2,4-dioxo-3-(2-oxo-ethyl)-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]acetamideYield 103.5%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of 1.5 g (2.93 mmol) of 2-(3-Allyl-3-methyl-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-[4-methoxyphenyl]acetamide, prepared as in Part C, in 10 mL of dioxane and 10 mL of H2O at 0° C. is added 3.13 g (14.63 mmol, 2 equiv.) of sodium periodate followed by the addition of 2 drops of osmium tetroxide solution (4% in H2O). The resulting suspension is stirred for 4 h and then diluted with 200 mL H2O and 200 mL of EtOAc. The organic phase is washed with H2O (2×250 mL) and a solution of Na2S2O3 (10%) and then dried (MgSO4), and the solvents removed in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 5/1 as eluent afforded 1.56 g of N-Isopropyl-N-[4-methoxyphenyl]-2-[3-methyl-2,4-dioxo-3-(2-oxo-ethyl)-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]acetamide as an oil: 1H NMR (CDCl3, 300 MHz) δ8.51 (m, 2H), 7.68 (d, 1H, J=9), 7.39-6.93 (m, 8H), 6.71 (d, 1H, J=8), 5.78-5.64 (m, 1H), 5.08-5.00 (m, 2H), 4.72 (d, 1H, J=16), 4.39 (d, 1H, J=17), 4.08 (m, 1H), 3.85 (s, 3H), 3.81-3.79 (m, 1H), 2.11 (d, 1H, J=8), 1.77 (s, 1H), 1.60 (s, 2H), 1.21-1.07 (m, 6H); low resolution MS (FAB)m/e 513 (MH+).

Workup

  1. washThe organic phase is washed with H2O (2×250 mL)
  2. dry with materiala solution of Na2S2O3 (10%) and then dried (MgSO4)
  3. customthe solvents removed in vacuo
  4. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-ccc4c6d0c2724483a689776fc2a0319f
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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