Diethyl (2-oxoethyl)phosphonate → HCID 86735062, compound

HRID 2071751Notes

Reaction equation

HRID 2071751 reaction equation
[CH3:1][CH2:2][C@H:3]1[O:17][C:15](=[O:16])[C@H:14]([CH3:18])[C@H:13]([O:19][C@@H:20]2[O:25][C@@H:24]([CH3:26])[C@H:23]([OH:27])[C@@:22]([O:29][CH3:30])([CH3:28])[CH2:21]2)[C@H:12]([CH3:31])[C@@H:11]([O:32][C@@H:33]2[O:38][C@H:37]([CH3:39])[CH2:36][C@H:35]([N:40]([CH3:42])[CH3:41])[C@H:34]2[OH:43])[C@@:10]([OH:45])([CH3:44])[CH2:9][C@@H:8]([CH3:46])[C@H:7]([NH2:47])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].[CH2:52]([O:54][P:55]([CH2:60][CH:61]=[O:62])([O:57][CH2:58][CH3:59])=[O:56])[CH3:53]>O1CCOCC1>[CH2:58]([O:57][P:55]([CH2:60][CH:61]=[O:62])([O:54][CH2:52][CH3:53])=[O:56])[CH3:59].[CH3:1][CH2:2][C@H:3]1[O:17][C:15](=[O:16])[C@H:14]([CH3:18])[C@H:13]([O:19][C@@H:20]2[O:25][C@@H:24]([CH3:26])[C@H:23]([OH:27])[C@@:22]([O:29][CH3:30])([CH3:28])[CH2:21]2)[C@H:12]([CH3:31])[C@@H:11]([O:32][C@@H:33]2[O:38][C@H:37]([CH3:39])[CH2:36][C@H:35]([N:40]([CH3:41])[CH3:42])[C@H:34]2[OH:43])[C@@:10]([OH:45])([CH3:44])[CH2:9][C@@H:8]([CH3:46])[C@H:7]([NH2:47])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

Participants

4

Reactant 2

HCID 342159Diethyl (2-oxoethyl)phosphonateHCID 53317778HCID 53317778, compound

Product 1

HCID 86735062HCID 86735062, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture consisting of 23 gm (0.03 mol) of erythromycylamine, 10 gm (0.055 mol) of diethylphosphonoacetaldehyde and 300 ml of absolute dioxane was stirred at room temperature for 24 hours. After evaporation of the solvent, the residue was taken up in 150 ml of hot acetonitrile, and the solution was mixed with 750 ml of water. Upon cooling 13 gm (43% of theory) of colorless crystals precipitated, which were dried at 80° C in vacuo. M.p. 110°-113° C (decomp.).

Workup

  1. customAfter evaporation of the solvent
  2. additionthe solution was mixed with 750 ml of water
  3. temperatureUpon cooling 13 gm (43% of theory) of colorless crystals
  4. customprecipitated
  5. customwhich were dried at 80° C in vacuo

Sources & evidence

ORD record
ord-0b07b3c84e3246478023cc4b4c47a44f
Source dataset
uspto-grants-1977_09
Patent number
US04048306

Reaction notes

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