Ethyl Acetate → HCID 86753586, compound

HRID 343092Notes

Reaction equation

HRID 343092 reaction equation
[CH2:1]([C:4]1([CH3:36])[C:10](=[O:11])[N:9]([CH2:12][C:13]([N:15]([CH:22]([CH3:24])[CH3:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[C:8]2[CH:25]=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:5]1=[O:35])[CH:2]=C.I([O-])(=O)(=O)=[O:38].[Na+].CCOC(C)=O>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:22]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](=[O:14])[CH2:12][N:9]1[C:10](=[O:11])[C:4]([CH3:36])([CH2:1][CH:2]=[O:38])[C:5](=[O:35])[N:6]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:7]2[CH:28]=[CH:27][CH:26]=[CH:25][C:8]1=2)([CH3:23])[CH3:24]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 10719568HCID 10719568, compoundHCID 23667635Sodium periodate

Product 1

HCID 86753586HCID 86753586, compoundYield 69.4%

Reagents, catalysts & solvents 3

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

Procedure

To a stirring solution of 200 mg (0.42 mmol) of 2-(3-Allyl-3-methyl-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide, prepared as in Intermediate 6, in 10 mL of 1,4-dioxane and 3 mL of H2O is added 0.5 mL of a 4% solution of osmium tetraoxide in H2O. The resulting solution is stirred 1 min, then 220 mg (1.03 mmol, 2.5 equiv) of sodium periodate is added. The reaction mixture is stirred 3 h at RT then poured into 25 mL of EtOAc and extracted with H2O (1×25 mL), sat. NaHSO3 (1×25 mL), dried (MgSO4), and the solvents removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 1/1 as eluent afforded 141 mg of the title compound as a white foam: 1H NMR (CDCl3, 300 MHz, mixture of conformations) δ9.65 (s, 0.8H), 9.40 (s, 0.2H), 7.50-7.03 (m, 13H), 6.83 (d, 0.8H), 6.75 (d, 0.2H), 5.07 (m, 0.8H), 4.96 (m, 0.2H), 4.41 (d, 1H), 4.02 (d, 1H), 2.96 (dd, 2H), 1.62 (s, 0.6H), 1.17 (s, 2.4H), 1.09 (m, 6H); low resolution MS (FAB) m/e 619 (MH+), 574.

Workup

  1. stirringThe reaction mixture is stirred 3 h at RT
  2. extractionextracted with H2O (1×25 mL), sat. NaHSO3 (1×25 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvents removed in vacuo
  5. customPurification of the crude material by silica gel flash column chromatography

Sources & evidence

ORD record
ord-591a3d435b2c4c4789c5dbc308550f56
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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