Methanol → 2-{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetic acid

HRID 2268435Notes

Reaction equation

HRID 2268435 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][C:36]#N)=[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-:38].[Na+].C[OH:41]>>[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][C:36]([OH:41])=[O:38])=[N:15][C:16]=2[NH:20][CH2:21][CH:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 599752932-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile

Product 1

HCID 599752822-{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetic acid

Procedure

A stirred solution of 2-{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile (preparation 30) (1.5 g, 3 mmol) in methanol (30 ml) and an aqueous 1 molar solution of sodium hydroxide (10 ml) was heated at reflux for 24 hr. The methanol was then removed under reduced pressure and the residual liquid diluted with more water and washed twice with ethyl acetate. The aqueous phase was acidified to pH<7 with a 1 molar aqueous citrc acid solution and then extracted twice with ethyl acetate. The extracts were combined, washed with brine and dried with anhydrous magnesium sulfate. The residue, after removal of the solvent under reduced pressure, was dissolved into diethyl ether and the solvent removed again twice under reduced pressure to give the title compound (1.25 g) as a foam. MS: 518 (M−H+).

Workup

  1. temperatureat reflux for 24 hr
  2. customThe methanol was then removed under reduced pressure
  3. additionthe residual liquid diluted with more water
  4. washwashed twice with ethyl acetate
  5. extractionextracted twice with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe residue, after removal of the solvent under reduced pressure
  9. dissolutionwas dissolved into diethyl ether
  10. customthe solvent removed again twice under reduced pressure

Sources & evidence

ORD record
ord-b9b1e6382cc04cbda5ebf4e8cd93ee2d
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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