Di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amine → (1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol

HRID 1696984Notes

Reaction equation

HRID 1696984 reaction equation
C(N(C(OC(C)(C)C)=O)[C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3[Cl:23])C=C1)(OC(C)(C)C)=O.COC1C=CC(C(N[C:50]2[N:58]=[C:57]([Cl:59])[N:56]=[C:55]3[C:51]=2[N:52]=[CH:53][N:54]3[C@@H:60]2[CH2:64][C@H:63]([N:65]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[C@@H:62]([OH:80])[C@H:61]2[OH:81])C2C=CC(OC)=CC=2)=CC=1>>[C:73]([N:65]([C:66]([O:68][C:69]([CH3:71])([CH3:72])[CH3:70])=[O:67])[C@H:63]1[CH2:64][C@@H:60]([N:54]2[CH:53]=[N:52][C:51]3[C:55]2=[N:56][C:57]([Cl:59])=[N:58][C:50]=3[Cl:23])[C@H:61]([OH:81])[C@@H:62]1[OH:80])([O:75][C:76]([CH3:78])([CH3:79])[CH3:77])=[O:74]

Participants

3

Reactant 2

HCID 58025018Di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amineHCID 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-diol

Product 1

HCID 57777515(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol

Procedure

The title compound is prepared from di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amine using a procedure analogous to that use to prepare (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. 1H nmr (CDCl3, 400 MHz); 8.35(s, 1H), 4.80(m, 1H), 4.70(m, 1H), 4.50(m, 1H), 3.85(m, 1H), 3.75(m, 1H), 3.10(m, 1H), 2.75(m, 1H), 2.55(m, 1H), 1.55(s, 18H), MS (ES+) m/e 504 (MH+).

Sources & evidence

ORD record
ord-474022f4af99423bb4e22bfcdfd77216
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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