N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide dihydrochloride → N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 215894Notes

Reaction equation

HRID 215894 reaction equation
Cl.Cl.[NH2:3][C@@H:4]1[CH2:8][CH2:7][N:6]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][N:15]3[C@@H:18]3[CH2:22][C@H:21]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[C@@H:20]([OH:28])[C@H:19]3[OH:29])=[C:11]([NH:30][CH2:31][CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:10]=2)[CH2:5]1>C(O)C>[NH2:3][C@@H:4]1[CH2:8][CH2:7][N:6]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][N:15]3[C@@H:18]3[CH2:22][C@H:21]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[C@@H:20]([OH:28])[C@H:19]3[OH:29])=[C:11]([NH:30][CH2:31][CH:32]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:10]=2)[CH2:5]1

Participants

3

Reactant 1

HCID 67022955N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide dihydrochloride

Product 1

HCID 59781437N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide dihydrochloride (ca. 7.7 mmol) is dissolved in minimal volume of a mixture of ethanol/saturated aqueous sodium carbonate solution until the pH of the solution is adjusted to pH 7 (ensuring the compound remains in solution). The solution is loaded onto an Isolute™ C18 column and washed through firstly with water and then MeOH. The fractions are combined and concentrated in vacuo and then further purified by repeating the above process to afford the title compound. LCMS (electrospray): m/z [MH+] 571

Workup

  1. washwashed through firstly with water
  2. concentrationconcentrated in vacuo
  3. customfurther purified

Sources & evidence

ORD record
ord-b5299e0c8fbe4c7f8b8a4fdca4170803
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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