(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(di-Boc-amino)-cyclopentane-1,2-diol → {(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionyl-carbamic acid tert-butyl ester

HRID 1696994Notes

Reaction equation

HRID 1696994 reaction equation
[C:1](OC(=O)N([C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3NC(CC)CC)C=C1)C(=O)CC)(C)(C)[CH3:2].COC1C=C[C:39]([CH:42]([NH:51][C:52]2[N:60]=[C:59]([Cl:61])[N:58]=[C:57]3[C:53]=2[N:54]=[CH:55][N:56]3[C@@H:62]2[CH2:66][C@H:65]([N:67]([C:75](OC(C)(C)C)=[O:76])[C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C@@H:64]([OH:82])[C@H:63]2[OH:83])[C:43]2[CH:48]=CC(OC)=CC=2)=[CH:38]C=1>>[C:71]([O:70][C:68](=[O:69])[N:67]([C@H:65]1[CH2:66][C@@H:62]([N:56]2[CH:55]=[N:54][C:53]3[C:57]2=[N:58][C:59]([Cl:61])=[N:60][C:52]=3[NH:51][CH:42]([CH2:43][CH3:48])[CH2:39][CH3:38])[C@H:63]([OH:83])[C@@H:64]1[OH:82])[C:75](=[O:76])[CH2:1][CH3:2])([CH3:72])([CH3:74])[CH3:73]

Participants

3

Reactant 2

HCID 86622623(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(di-Boc-amino)-cyclopentane-1,2-diolHCID 86622634{(1S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-cyclopent-2-enyl}-propionyl-carbamic acid tert-butyl ester

Product 1

HCID 86622635{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionyl-carbamic acid tert-butyl ester

Procedure

The title compound is prepared from {(1S,4R)-4-[2-chloro-6-(1-ethyl-propylamino)-purin-9-yl]-cyclopent-2-enyl}-propionyl-carbamic acid tert-butyl ester using a procedure analogous to that of (1R,2S,3R,5S)-3-(6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(di-Boc-amino)-cyclopentane-1,2-diol (see Example 1). Purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA). 1H nmr (MeOD, 400 MHz); 8.10(s, 1H), 4.80(m, 1H), 4.65(m, 1H), 4.35(m, 1H), 4.20(m, 1H), 2.85(m, 2H), 2.60(m, 1H), 2.35(m, 1H), 1.70(m, 2H), 1.65(s, 9H), 1.60(m, 2H), 1.15(t, 3H), 0.95(t, 6H).

Workup

  1. customPurification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA)

Sources & evidence

ORD record
ord-59b1d89450e84715b45dd8e2e0e1d637
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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