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Acetic Acid → (2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{[(1-methyl-4-piperidinyl)oxy]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268398
Notes
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Reaction equation

HRID 2268398 reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][O:50][CH:51]1[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]1)=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:37]1([CH:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:35][NH:34][C:30]2[N:29]=[C:28]([CH2:49][O:50][CH:51]3[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]3)[N:27]=[C:26]3[C:31]=2[N:32]=[CH:33][N:25]3[C@H:10]2[C@H:9]([OH:8])[C@H:13]([OH:14])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium Fluoride2×HCID 69534109N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[(1-methyl-4-piperidinyl)oxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

Product 1

HCID 59975327(2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{[(1-methyl-4-piperidinyl)oxy]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol
Yield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[(1-methyl-4-piperidinyl)oxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (68 mg, 0.08 mmol) (preparation 49) was dissolved in stirred tetrahydrofuran (10 ml), then acetic acid (0.2 ml, 0.2 mmol) added followed by a 1 molar solution of tetra-n-butylammonium fluoride (0.2 ml, 0.2 mmol). The reaction mixture was stirred at room temperature for 1 hr and then more 1 molar solution of tetrabutylammonium fluoride (0.5 ml, 0.5 mmol) was added. The reaction mixture was stirred for another hour and then partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The ethyl acetate phase was separated, washed with brine and dried with anhydrous sodium sulfate. This was evaporated to give a clear oil which was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (95:5) increasing in polarity to dichloromethane:methanol:ammonia (90:10:1) to give the title compound (20 mg) as a foam. MS: 589 (MH+).

Workup

  1. stirringThe reaction mixture was stirred for another hour
  2. custompartitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  3. customThe ethyl acetate phase was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThis was evaporated
  7. customto give a clear oil which
  8. customwas purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (95:5)
  9. temperatureincreasing in polarity to dichloromethane:methanol:ammonia (90:10:1)

Sources & evidence

ORD record
ord-15b4a76cbd1846b5aed908f24b373bea
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326359B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes