Sodium Iodide → HCID 66630794, compound

HRID 2382392Notes

Reaction equation

HRID 2382392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)([OH:36])[CH2:9][NH:10][C:11]2[N:19]=[C:18](Cl)[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:21]2[CH2:25][C@H:24]([NH:26][C:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:28])[C@@H:23]([OH:34])[C@H:22]2[OH:35])=[CH:4][CH:3]=1.[C:44]([NH:51][C@@H:52]1[CH2:56][CH2:55][NH:54][CH2:53]1)([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45].[I-].[Na+]>C(#N)C>[Cl:43][C:40]1[CH:39]=[CH:38][C:37]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:36])[CH2:9][NH:10][C:11]2[N:19]=[C:18]([N:54]3[CH2:55][CH2:56][C@@H:52]([NH:51][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:53]3)[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:21]2[CH2:25][C@H:24]([NH:26][C:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:28])[C@@H:23]([OH:34])[C@H:22]2[OH:35])=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 86647547HCID 86647547, compound

Product 1

HCID 66630794HCID 66630794, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of acetic acid ((1S,2R,3S,4R)-4-{6-[2,2-bis-(4-chloro-phenyl)-2-hydroxy-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentylcarbamoyl)-methyl ester (intermediate ZL; 1 equivalent) and (3R)-(+)-3-(Boc-amino)pyrrolidine (4 equivalents) in acetonitrile is treated with a catalytic amount of sodium iodide and then heated using microwave radiation in a Personal Chemistry Emrys™ Optimizer microwave reactor at 160° C. After 1 hour, the solvent is removed in vacuo; purification by column chromatography/crystallisation affords the title compound.

Workup

  1. temperatureheated
  2. customat 160° C
  3. customthe solvent is removed in vacuo
  4. custompurification
  5. customby column chromatography/crystallisation

Sources & evidence

ORD record
ord-53b6dc1e6ace444dbcb2660a70eff70c
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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