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Phenylacetyl chloride → 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-phenylacetamide

HRID 2268341
Notes
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Reaction equation

HRID 2268341 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.C(N(CC)CC)C.[C:44]1([CH2:50][C:51](Cl)=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>ClCCl>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13][C@H:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([CH2:2][NH:1][C:51](=[O:52])[CH2:50][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 9916870N-{[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl]methyl}-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (220 mg, 0.45 mmol) in dichloromethane (10 ml) was treated with triethylamine (0.38 ml, 2.70 mmol) and phenylacetylchloride (280 mg, 1.80 mmol) at 0° C. and the resultant mixture stirred for 15 min. The mixture was then stirred at room temperature for 72 hr. The solvent was removed under reduced pressure and methanol (20 ml), saturated with ammonia gas, added. The resultant mixture was stirred at room temperature for 2 hr, treated with 2 molar aqueous sodium hydroxide (10 ml) and then left standing at room temperature for 24 hr. The methanol was removed under reduced pressure and the aqueous layer extracted with dichloromethane (×3). The combined organic layers were washed with water (×2), dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was dissolved in 1,4-dioxan (6 ml), 0.88 aqueous ammonia solution (8 ml) added and the mixture stirred at room temperature for 10 days. The 1,4-dioxan was removed under reduced pressure and the aqueous layer extracted with dichloromethane (×3).

Workup

  1. customThe solvent was removed under reduced pressure and methanol (20 ml), saturated with ammonia gas
  2. additionadded
  3. stirringThe resultant mixture was stirred at room temperature for 2 hr
  4. additiontreated with 2 molar aqueous sodium hydroxide (10 ml)
  5. waitleft
  6. waitstanding at room temperature for 24 hr
  7. customThe methanol was removed under reduced pressure
  8. extractionthe aqueous layer extracted with dichloromethane (×3)
  9. washThe combined organic layers were washed with water (×2)
  10. dry with materialdried with anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure
  13. dissolutionThe residue was dissolved in 1,4-dioxan (6 ml)
  14. addition0.88 aqueous ammonia solution (8 ml) added
  15. stirringthe mixture stirred at room temperature for 10 days
  16. customThe 1,4-dioxan was removed under reduced pressure
  17. extractionthe aqueous layer extracted with dichloromethane (×3)

Sources & evidence

ORD record
ord-3c4111335b6543b980e2ae5dd3f2cc60
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326359B1

Reaction notes

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