2-Chloroadenosine → 2-[2-(1,4-Dioxaspiro[4.5]dec-8-yl)ethylamino]adenosine

HRID 1087017Notes

Reaction equation

HRID 1087017 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[O:21]1[C:25]2([CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][NH2:33])[CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1>>[O:21]1[C:25]2([CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][NH:33][C:2]3[N:3]=[C:4]([NH2:20])[C:5]4[N:6]=[CH:7][N:8]([C:18]=4[N:19]=3)[C@@H:9]3[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]3[OH:11])[CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 89742-ChloroadenosineHCID 100582342-(1,4-Dioxa-spiro[4.5]dec-8-YL)-ethylamine

Product 1

HCID 150366472-[2-(1,4-Dioxaspiro[4.5]dec-8-yl)ethylamino]adenosine

Procedure

A mixture of 2-chloroadenosine (0.3 g) and 1,4-dioxaspiro[4.5]decane-8-ethanamine (1.0 g) is heated under nitrogen at 140° for 6 hours. It is evaporated to dryness at reduced pressure, the residue is dissolved in ethanol, the solution is treated with propylene oxide (2 ml) and stirred 4 hours. The precipitate is collected, washed with ethanol and dried in vacuo to give 2-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethylamino]adenosine, [alpha]D25 =-27.3° (MeOH), m.p. 133°-137°.

Workup

  1. temperatureis heated under nitrogen at 140° for 6 hours
  2. customIt is evaporated to dryness at reduced pressure
  3. dissolutionthe residue is dissolved in ethanol
  4. additionthe solution is treated with propylene oxide (2 ml)
  5. customThe precipitate is collected
  6. washwashed with ethanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-16b72249490b4e04a53a74e7e09565ee
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

Loading…