HCID 44185157, compound → HCID 66630131, compound

HRID 2382489Notes

Reaction equation

HRID 2382489 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:10][C:11]([C@@H:13]1[C@@H:17]([OH:18])[C@@H:16]([OH:19])[C@H:15]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][C:23]([N:44]2[CH2:48][CH2:47][C@@H:46]([NH2:49])[CH2:45]2)=[N:24][C:25]=3[NH:29][CH2:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:14]1)=[O:12])[CH3:9].C1([O:56][C:57](=O)[NH:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[C:62]([OH:66])[CH:61]=2)C=CC=CC=1>CO>[CH2:8]([NH:10][C:11]([C@@H:13]1[C@@H:17]([OH:18])[C@@H:16]([OH:19])[C@H:15]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][C:23]([N:44]2[CH2:48][CH2:47][C@@H:46]([NH:49][C:57]([NH:58][CH2:59][C:60]4[CH:65]=[CH:64][CH:63]=[C:62]([OH:66])[CH:61]=4)=[O:56])[CH2:45]2)=[N:24][C:25]=3[NH:29][CH2:30][CH:31]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:14]1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 44185157HCID 44185157, compoundHCID 66630764HCID 66630764, compound2×

Product 1

HCID 66630131HCID 66630131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,3S,4R,5R)-5-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide trifluoroacetate (Intermediate E) and (3-Hydroxy-benzyl)-carbamic acid phenyl ester (Intermediate UA) are dissolved in methanol and TEA. The reaction mixture is heated using microwave radiation at 100° C. for 30 minutes in the Personal Chemistry Emrys™ Optimizer microwave reactor. The reaction mixture is concentrated in vacuo and purified by C-18 reverse phase column chromatography eluting with acetonitrile:water (0.1% TFA) (gradient 0-100% acetonitrile) to afford the titled compound.

Workup

  1. temperatureThe reaction mixture is heated
  2. customat 100° C.
  3. customfor 30 minutes
  4. concentrationThe reaction mixture is concentrated in vacuo
  5. custompurified by C-18 reverse phase column chromatography
  6. washeluting with acetonitrile

Sources & evidence

ORD record
ord-8ad5305747264544b2f6feb7a6ecfcf2
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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