Potassium Hydroxide → HCID 23702367, compound

HRID 2268399Notes

Reaction equation

HRID 2268399 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][CH3:10])[O:4][C@H:3]1[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][C:14]([CH2:35][NH:36][S:37](CC(C)C)(=[O:39])=[O:38])=[N:15][C:16]=2[NH:20][CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-:44].[K+:45]>C(O)(C)C>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][CH3:10])[O:4][C@H:3]1[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][C:14]([CH2:35][N:36]([CH2:21][CH:22]([CH3:29])[CH3:23])[S:37]([O-:38])(=[O:44])=[O:39])=[N:15][C:16]=2[NH:20][CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[K+:45]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9830350HCID 9830350, compound

Product 1

HCID 23702367HCID 23702367, compoundYield 145.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulfonamide (example 15) (1.9 g, 3.11 mmol) was dissolved into isopropyl alcohol (20 ml) and a 4 molar solution of potassium hydroxide (0.9 ml, 3.11 mmol) added. The isopropyl alcohol was removed by evaporation under reduced pressure and more isopropyl alcohol (20 ml) added to the residue, then the solvent removed under reduced pressure again. The residue was suspended in isopropyl alcohol (160 ml) and then the suspension heated under reflux for 1 hr. The resulting suspension was allowed to cool and then filtered. The white solid was washed with a little isopropyl alcohol and then dried. This gave the title compound (1.5 g) as a white crystalline solid m.p. 231° C.

Workup

  1. customThe isopropyl alcohol was removed by evaporation under reduced pressure and more isopropyl alcohol (20 ml)
  2. additionadded to the residue
  3. customthe solvent removed under reduced pressure again
  4. temperaturethe suspension heated
  5. temperatureunder reflux for 1 hr
  6. temperatureto cool
  7. filtrationfiltered
  8. washThe white solid was washed with a little isopropyl alcohol
  9. customdried

Sources & evidence

ORD record
ord-f9250a36d3c64da7b96843a6ca6b1893
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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