1,4-Dioxane → HCID 86735061, compound

HRID 2071749Notes

Reaction equation

HRID 2071749 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].C(OC(OCC)C(C(=O)C)O)C.O1CCOCC1>O>[C:3]([CH:4]([OH:51])[CH:5]=[O:49])(=[O:17])[CH3:2].[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

5

Reactant 3

HCID 312751,4-DioxaneHCID 21412313HCID 21412313, compoundHCID 53317778HCID 53317778, compound

Product 1

HCID 86735061HCID 86735061, compoundYield 191.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of 2.3 gm (0.003 mol) of erythromycylamine, 1.1 gm (0.006 mol) of acetylglycolaldehyde-diethylacetal, 20 ml of dioxane, 2 ml of water and 12 gm of Dowex 50 W was stirred at room temperature. After 6 hours of stirring the ion exchanger was filtered off and washed with dioxane. The filtrate was evaporated, and the residue was purified by column chromatography (basic aluminum oxide, activity stage 3; chloroform/methanol = 4:1). The fraction with an Rf -value of 0.6 was evaporated and brought to crystallization by treatment with chloroform/ether. 2.4 gm of colorless crystals, m.p. 105°-110° C, was obtained.

Workup

  1. stirringAfter 6 hours of stirring the ion exchanger
  2. filtrationwas filtered off
  3. washwashed with dioxane
  4. customThe filtrate was evaporated
  5. customthe residue was purified by column chromatography (basic aluminum oxide, activity stage 3; chloroform/methanol = 4:1)
  6. customThe fraction with an Rf -value of 0.6 was evaporated
  7. custombrought to crystallization by treatment with chloroform/ether

Sources & evidence

ORD record
ord-5efd07e733854594854df7fa7d36bea2
Source dataset
uspto-grants-1977_09
Patent number
US04048306

Reaction notes

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