Sodium Iodide → HCID 66630819, compound

HRID 1882610Notes

Reaction equation

HRID 1882610 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:45])[C:10]([NH:12][C@H:13]1[CH2:17][C@@H:16]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][C:21](Cl)=[N:22][C:23]=3[NH:27][CH2:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:15]([OH:43])[C@@H:14]1[OH:44])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:46]([NH:53][C@@H:54]1[CH2:58][CH2:57][NH:56][CH2:55]1)([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47].[I-].[Na+]>C(#N)C>[C:49]([O:48][C:46](=[O:47])[NH:53][C@@H:54]1[CH2:58][CH2:57][N:56]([C:21]2[N:20]=[C:19]3[C:24]([N:25]=[CH:26][N:18]3[C@@H:16]3[CH2:17][C@H:13]([NH:12][C:10](=[O:11])[C@H:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH3:45])[C@@H:14]([OH:44])[C@H:15]3[OH:43])=[C:23]([NH:27][CH2:28][CH:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:22]=2)[CH2:55]1)([CH3:52])([CH3:50])[CH3:51]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 86647565(R)-2-benzyloxy-N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Product 1

HCID 66630819HCID 66630819, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of (R)-2-benzyloxy-N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (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-34a331a3ebf840719371eb20c526dfcd
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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