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Trimethylsilyl triflate → Methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetraazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate

HRID 1168301
Notes
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Reaction equation

HRID 1168301 reaction equation
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]([O:32][C@H:33]1[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[CH:36](OC(=O)C)[O:35][C@@H:34]1[C:46]1[N:47]=[N:48][N:49]([CH2:51][CH3:52])[N:50]=1)(=[O:31])[CH3:30].C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClC(Cl)(Cl)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:39]([O:38][C@@H:37]1[C@H:33]([O:32][C:29](=[O:31])[CH3:30])[C@@H:34]([C:46]2[N:47]=[N:48][N:49]([CH2:51][CH3:52])[N:50]=2)[O:35][C@H:36]1[N:14]1[CH:13]=[N:12][C:11]2[C:15]1=[N:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[N:18][C:10]=2[NH:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:41])[CH3:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 11302289(2R,3R,4R)-4,5-bis(acetoxy)-2-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetateHCID 178418823HCID 178418823, compound

Product 1

HCID 59094502Methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetraazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylateYield 62.7%

Reagents, catalysts & solvents

3
HCID 1140TolueneSolventHCID 62781,1,1-TrichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 29) (0.4 g, 1.07 mmol) in 1,1,1-trichloroethane (25 ml) was treated with N,O-bis(trimethylsilylacetamide) (1.6 ml, 6.54 mmol) and the mixture was heated under reflux for one hour. The solvent was removed under reduced pressure and the residue was twice azeotroped with toluene. The residue was dissolved in toluene (5 ml) and treated sequentially with a solution of (2R,3R,4R)-4,5-bis(acetyloxy)-2-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (WO-A-9967265) (0.45 g, 1.31 mmol) in toluene (20 ml) and then trimethylsilyltriflate (0.25 ml, 1.37 mmol). The mixture was heated under reflux for 3 hours and then allowed to stand at room temperature overnight. The solution was diluted with ethyl acetate (40 ml), washed sequentially with saturated aqueous sodium hydrogen carbonate solution (20 ml) and brine (20 ml), dried (anhydrous magnesium sulphate) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:ethyl acetate (80:20 by volume) gradually changing to dichloromethane:ethyl acetate (60:40 by volume) to afford the title compound (0.44 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was twice azeotroped with toluene
  5. dissolutionThe residue was dissolved in toluene (5 ml)
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 3 hours
  8. washwashed sequentially with saturated aqueous sodium hydrogen carbonate solution (20 ml) and brine (20 ml)
  9. dry with materialdried (anhydrous magnesium sulphate)
  10. customevaporated under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:ethyl acetate (80:20 by volume)

Sources & evidence

ORD record
ord-9b1af8abcfa04879b3666d659fbd159d
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06624158B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes