Triethylamine → {9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

HRID 2268411Notes

Reaction equation

HRID 2268411 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Si:6]([O:13][C@@H:14]1[C@H:18]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C@@H:17]([CH2:27][O:28][CH3:29])[O:16][C@H:15]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][C:33]([CH2:54][OH:55])=[N:34][C:35]=2[NH:39][CH2:40][CH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:55][CH2:54][C:33]1[N:32]=[C:31]2[C:36]([N:37]=[CH:38][N:30]2[C@H:15]2[C@H:14]([O:13][Si:6]([C:9]([CH3:11])([CH3:12])[CH3:10])([CH3:7])[CH3:8])[C@H:18]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:22])[CH3:21])[C@@H:17]([CH2:27][O:28][CH3:29])[O:16]2)=[C:35]([NH:39][CH2:40][CH:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:34]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 69534107{9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanol

Product 1

HCID 86757641{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.6 ml, 7.7 mmol) was slowly added to a stirred solution of {9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanol (4.22 g, 5.87 mmol) (preparation 15) and triethylamine (1.2 ml, 8.62 mmol) in dichloromethane (50 ml) and the mixture stirred at room temperature for 30 minutes. Triethylamine (1 ml, 7.2 mmol) and methanesulfonyl chloride (0.5 ml, 6.4 mmol) were then added and stirring continued for a further 15 minutes. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (1:3) changing to ethyl acetate:pentane (1:1) to afford the title compound as a gum (4.52 g). MS: 820 (MNa+).

Workup

  1. stirringstirring
  2. waitcontinued for a further 15 minutes
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (1:3)

Sources & evidence

ORD record
ord-e4ff233e0a774920be691ad90f3163aa
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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