Potassium Carbonate → (2R,3R,4S,5S)-2-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3,4-diol

HRID 655121Notes

Reaction equation

HRID 655121 reaction equation
Cl.C([O:5][C@@H:6]1[C@@H:10]([C:11]2[O:15][N:14]=[C:13]([CH2:16][CH3:17])[CH:12]=2)[O:9][C@@H:8]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][C:21]([Cl:38])=[N:22][C:23]=3[NH:27][C@@H:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][OH:30])[C@@H:7]1[O:39]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)(Cl)Cl.C(Cl)Cl.O>[CH2:31]([C@H:28]([NH:27][C:23]1[N:22]=[C:21]([Cl:38])[N:20]=[C:19]2[C:24]=1[N:25]=[CH:26][N:18]2[C@H:8]1[C@H:7]([OH:39])[C@H:6]([OH:5])[C@@H:10]([C:11]2[O:15][N:14]=[C:13]([CH2:16][CH3:17])[CH:12]=2)[O:9]1)[CH2:29][OH:30])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86623488Acetic acid (2R,3R,4R,5S)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethyl amino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester hydrochloride

Product 1

HCID 86634603(2R,3R,4S,5S)-2-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3,4-diol

Reagents, catalysts & solvents 2

HCID 21584188Chloroform methanolSolventHCID 21908982Water methylene chlorideSolvent

Procedure

A solution of acetic acid (2R,3R,4R,5S)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethyl amino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)tetrahydro-furan-3-yl ester hydrochloride (Step AC1) (1.194 g, 2.02 mmol) in MeOH/chloroform (4 at, 3:1 MeOH/chloroform) is treated with saturated potassium carbonate solution (10 mL). After stirring at RT overnight, the reaction mixture is diluted with DCM/water and the organic portion is separated. The organic portion is concentrated in vacuo to afford the title compound. (MH+501)

Workup

  1. customthe organic portion is separated
  2. concentrationThe organic portion is concentrated in vacuo

Sources & evidence

ORD record
ord-8801b82fc46b4f63b8665b24a5a8eb93
Source dataset
uspto-grants-2011_12
Patent number
US08071565B2

Reaction notes

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