1,4-Dioxane → HCID 86735062, compound

HRID 2071750Notes

Reaction equation

HRID 2071750 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[O:53][CH:54](OC)[CH2:55][P:56]([O:61][CH2:62][CH3:63])([O:58][CH2:59][CH3:60])=[O:57].O1CCOCC1>O>[CH2:62]([O:61][P:56]([CH2:55][CH:54]=[O:53])([O:58][CH2:59][CH3:60])=[O:57])[CH3:63].[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 3248918Diethyl (2,2-dimethoxyethyl)phosphonateHCID 53317778HCID 53317778, compound

Product 1

HCID 86735062HCID 86735062, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of 2.3 gm (0.003mol) of erythromycylamine, 1.4 gm (0.006 mol) of diethylphosphonoacetaldehyde-dimethylacetal, 20 ml of dioxane, 2 ml of water and 12 gm of Dowex W 50 was stirred at room temperature. After 6 hours of stirring the ion exchanger was filtered off and washed with dioxane. Water was added to the filtrate until crystallization started. The white product was suction-filtered off, washed with aqueous dioxane and dried. Yield: 1.4 gm (52% of theory), m.p. 110°-113° C (decomp.).

Workup

  1. stirringAfter 6 hours of stirring the ion exchanger
  2. filtrationwas filtered off
  3. washwashed with dioxane
  4. additionWater was added to the filtrate until crystallization
  5. filtrationThe white product was suction-filtered off
  6. washwashed with aqueous dioxane
  7. customdried

Sources & evidence

ORD record
ord-165a31c5c2df42e0acff9dd06e7a6545
Source dataset
uspto-grants-1977_09
Patent number
US04048306

Reaction notes

Loading…