HCID 86643678, compound → HCID 86643677, compound

HRID 215882Notes

Reaction equation

HRID 215882 reaction equation
C([O:8][C:9](=O)[NH:10][CH2:11][C:12](=[O:46])[NH:13][C@H:14]1[CH2:18][C@@H:17]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][C:22]([Cl:43])=[N:23][C:24]=3[NH:28][CH2:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:16]([OH:44])[C@@H:15]1[OH:45])C1C=CC=CC=1>CCO>[Cl:43][C:22]1[N:21]=[C:20]2[C:25]([N:26]=[CH:27][N:19]2[C@@H:17]2[CH2:18][C@H:14]([N:13]3[C:12](=[O:46])[CH2:11][NH:10][C:9]3=[O:8])[C@@H:15]([OH:45])[C@H:16]2[OH:44])=[C:24]([NH:28][CH2:29][CH:30]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:23]=1

Participants

3

Reactant 1

HCID 86643678HCID 86643678, compound

Product 1

HCID 86643677HCID 86643677, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

({(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl)-carbamic acid benzyl ester (Intermediate UA) is dissolved in EtOH and purged with argon and Pd/C is added. The reaction mixture is placed under a positive pressure of H2(g) (0.35 Barr) at RT over night. The reaction mixture is filtered through celite and reduced in vacuo. Intermediate VA is obtained after purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA).

Workup

  1. custompurged with argon and Pd/C
  2. additionis added
  3. waitThe reaction mixture is placed under a positive pressure of H2(g) (0.35 Barr) at RT over night
  4. filtrationThe reaction mixture is filtered through celite
  5. customIntermediate VA is obtained
  6. customafter purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA)

Sources & evidence

ORD record
ord-cd42374b53fb4f979009dfde9bd53ef7
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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