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Benzyl mercaptan → (2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268401
Notes
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Reaction equation

HRID 2268401 reaction equation
CS(O[CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]=1)(=O)=O.[C:41]1([CH2:47][SH:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(N(CC)CC)C>ClCCl>[CH2:47]([S:48][CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:8]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Product 1

HCID 59975291(2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 31.6%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (300 mg, 0.53 mmol) (preparation 25) was dissolved in stirred dichloromethane (4 ml) and phenylmethanethiol (0.13 ml, 1.05 mmol) and triethylamine (0.15 ml, 1.05 mmol) added. The reaction mixture was stirred for 48 hr at room temperature and then the solvent removed under reduced pressure. The residue was partitioned between methanol (100 ml) and hexane (100 ml) and the methanol layer washed with a further amount of hexane (100 ml). The solvent was then removed under reduced pressure from the methanol layer. The residue was purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:2) increasing in polarity to ethyl acetate:methanol (98:2). This gave title compound (100 mg) as a foam. MS: 599 (MH+).

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue was partitioned between methanol (100 ml) and hexane (100 ml)
  3. washthe methanol layer washed with a further amount of hexane (100 ml)
  4. customThe solvent was then removed under reduced pressure from the methanol layer
  5. customThe residue was purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:2)
  6. temperatureincreasing in polarity to ethyl acetate:methanol (98:2)

Sources & evidence

ORD record
ord-d4a9114221404178bd6de576db947094
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326359B1

Reaction notes

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