2-Methylbenzenesulfonic acid → {(R)-1-[9-((3aS,4R,6S,6aR)-2,2-Dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester

HRID 2382363Notes

Reaction equation

HRID 2382363 reaction equation
[CH2:1]([O:8][C:9](=[O:52])[NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[C@@H:25]3[CH2:29][C@H:28]([NH:30][C:31](=[O:34])[CH2:32][CH3:33])[C@@H:27]([OH:35])[C@H:26]3[OH:36])=[C:18]([NH:37][CH2:38][CH:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:17]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:53]1(C)[C:54](S(O)(=O)=O)=CC=C[CH:58]=1.[OH-].[NH4+]>CC(C)=O.COC(OC)(C)C>[CH2:1]([O:8][C:9](=[O:52])[NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[C@H:25]3[C@H:26]4[C@H:27]([O:35][C:53]([CH3:54])([CH3:58])[O:36]4)[C@@H:28]([NH:30][C:31](=[O:34])[CH2:32][CH3:33])[CH2:29]3)=[C:18]([NH:37][CH2:38][CH:39]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:17]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 14923Ammonium HydroxideHCID 24863132{(R)-1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester

Product 1

HCID 66630309{(R)-1-[9-((3aS,4R,6S,6aR)-2,2-Dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of {(R)-1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester (0.63 g, 0.89 mmol) in acetone (10 ml) and 2,2-dimethyloxypropane (5 ml) is treated with toluenesulfonic acid (ca. 60 mg) and then stirred at room temperature overnight. The mixture is basified using ammonium hydroxide and the solvent is removed in vacuo. The crude product is partitioned between DCM and water and the organic portion is washed with brine, dried over MgSO4, filtered and the solvent is removed in vacuo to give the title compound. [MH+ 745].

Workup

  1. customthe solvent is removed in vacuo
  2. customThe crude product is partitioned between DCM and water
  3. washthe organic portion is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-09ec5ac157c24b81b3dc5d26fc78a910
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

Loading…