Reaction #742303

ord-8801b82fc46b4f63b8665b24a5a8eb93

Reaction equation

CCc1cc([C@H]2O[C@@H](n3cnc4c(N[C@H](CO)Cc5ccccc5)nc(Cl)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)on1.Cl
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
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CCc1cc([C@H]2O[C@@H](n3cnc4c(N[C@H](CO)Cc5ccccc5)nc(Cl)nc43)[C@H](O)[C@@H]2O)on1
title compound
CCc1cc([C@H]2O[C@@H](n3cnc4c(N[C@H](CO)Cc5ccccc5)nc(Cl)nc43)[C@H](O)[C@@H]2O)on1
(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

Reactants

CCc1cc([C@H]2O[C@@H](n3cnc4c(N[C@H](CO)Cc5ccccc5)nc(Cl)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)on1.Cl
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
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagents

None

Solvents

ClCCl.O
DCM water
CO.ClC(Cl)Cl
MeOH chloroform

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe organic portion is separated
  2. 2
    ConcentrationThe organic portion is concentrated in vacuo

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)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08071565B2uspto-grants-2011_12