Oxygen → HCID 57025855, compound

HRID 728885Notes

Reaction equation

HRID 728885 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([CH:11]=[C:12]([CH3:20])[CH2:13][P:14]([O:18][CH3:19])([O:16][CH3:17])=[O:15])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[OH:23].[Na+].O=O>O.O1CCOCC1.[Pt].[Pt]=O>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH:11]=[C:12]([CH3:20])[CH2:13][P:14]([O:16][CH3:17])([O:18][CH3:19])=[O:15])[C:9]([OH:23])=[O:10])=[O:21])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 3

HCID 977OxygenHCID 516892Sodium BicarbonateHCID 57187635HCID 57187635, compound

Product 1

HCID 57025855HCID 57025855, compoundYield 22.7%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.66 g of 8 and 0.2 g of sodium hydrogen carbonate in 20 ml of water and 2 ml of dioxane there is added a suspension of platinum prepared by hydrogenation of 313 mg of platinum oxide in 50 ml of water. In a cylindrical apparatus, oxygen is passed through the mixture from bottom to top at 55° by means of a glass frit, with vigorous stirring. The mixture is filtered and washed with water, and the filtrate is extracted five times with 100-150 ml of ethyl acetate each time. Concentration of the extracts by evaporation yields 220 mg of educt 5. 1 gof Amberlyst® 15 (strongly acidic) is added to the aqueous phase, whichis then filtered and concentrated by evaporation in vacuo at 40°. Purification as in f,a) yields 156 mg of 9. 1H-NMR (300 MHz, CDCl3): 1.43 (s, (CH3)3C); 1.96 (d, J=3 Hz, CH3 --C(4)); 2.55 and 2.71 (2 d×d, J=22 and 15, 2H--C(5)); 3.75 and 3.76(2 d, J=11, 2 OCH3); 4.97 (m, H--C(2)); 5.25-5.45 (m, NH and H--C(3)).

Workup

  1. customto top at 55° by means of a glass frit, with vigorous stirring
  2. filtrationThe mixture is filtered
  3. washwashed with water
  4. extractionthe filtrate is extracted five times with 100-150 ml of ethyl acetate each time
  5. customConcentration of the extracts by evaporation
  6. customyields 220 mg of educt 5
  7. addition1 gof Amberlyst® 15 (strongly acidic) is added to the aqueous phase, whichis
  8. filtrationthen filtered
  9. concentrationconcentrated by evaporation in vacuo at 40°
  10. customPurification as in f,a)

Sources & evidence

ORD record
ord-0a3ae416555b461e86e7ff34e7398e95
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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