Sodium Bicarbonate → HCID 69782382, compound

HRID 1420799Notes

Reaction equation

HRID 1420799 reaction equation
[OH:1][C:2]1(CO)[CH:7]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[NH:11][C:10]2=[CH:29][C:30]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)=[O:31])[CH2:6][CH:5]2[CH2:40][CH:3]1[C:4]2([CH3:42])[CH3:41].I([O-])(=O)(=O)=O.[Na+].C([O-])(O)=O.[Na+]>Cl>[CH3:41][C:4]1([CH3:42])[CH:3]2[CH2:40][CH:5]1[CH2:6][CH:7]([CH2:8][N:9]1[C:13](=[O:14])[C:12]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[NH:11][C:10]1=[CH:29][C:30]([C:32]1[CH:33]=[CH:34][C:35]([C:36]#[N:37])=[CH:38][CH:39]=1)=[O:31])[C:2]2=[O:1]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 69783257HCID 69783257, compound

Product 1

HCID 69782382HCID 69782382, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-{[1-(2-Hydroxy-2-hydroxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-5-oxo-4,4-bis-pyridin-4-ylmethyl-imidazolidin-2-ylidene]-acetyl}-benzonitrile (540 mg, 0.914 mmol), as prepared in example 48, was dissolved in 0.1 N HCl (5 ml). To this solution was added sodium periodate (235 mg, 1.10 mmol). After stirring at ambient temperature for 16 hours, the pH of the reaction was adjusted to 8 using NaHCO3. The reaction was then partitioned between CH2Cl2 and saturated NaHCO3. The CH2Cl2 was dried over Na2SO4, filtered and concentrated under vacuum to give a golden foam which was then chromatographed on silica gel using 60% acetone in hexanes to give 331 mg of the titled compound as a brown foam: C.I. m/z 560 [M+1]; 1H NMR (CDCl3)δ 10.36 (br s, 1H), 8.48 (m, 4H), 7.94 (d, J=8.3 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.14 (m, 4H), 5.49 (s, 1H), 3.46 (m, 2H), 3.29 (m, 2H), 3.09 (m, 2H), 2.52 (m, 2H), 2.24 (m, 1H), 2.18 (m, 1H), 1.49 (m, 1H), 1.29 (s, 3H), 1.19 (d, J=8.9 Hz, 1H), 0.89 (m, 1H), 0.76 (s, 3H).

Workup

  1. customThe reaction was then partitioned between CH2Cl2 and saturated NaHCO3
  2. dry with materialThe CH2Cl2 was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a golden foam which
  6. customwas then chromatographed on silica gel using 60% acetone in hexanes

Sources & evidence

ORD record
ord-3fda591c784c446d9cd23d1470b1138f
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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