(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol → (1R,2S,3R,5S)-3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diol

HRID 215846Notes

Reaction equation

HRID 215846 reaction equation
[C:1]([N:8]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:24])=[N:18][C:19]=3Cl)[C@H:11]([OH:25])[C@@H:10]1[OH:26])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1N=C2C(N=CN2[C@@H]2C[C@H](N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)C=C2)=C([NH:64][CH2:65][CH:66]([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)N=1>>[Cl:24][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@@H:12]2[CH2:13][C@H:9]([N:8]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C@@H:10]([OH:26])[C@H:11]2[OH:25])=[C:19]([NH:64][CH2:65][CH:66]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[N:18]=1

Participants

3

Reactant 2

HCID 57777515(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diolHCID 59418857{2-Chloro-9-[(1R,4S)-4-(di-Boc-amino)-cyclopent-2-enyl]-9H-purin-6-yl}-(2,2-diphenyl-ethyl)amine

Product 1

HCID 59418824(1R,2S,3R,5S)-3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diol

Procedure

The title compound is prepared analogously to (1S,2R,3S,5R)-3-(di-Boc-amino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol by replacing di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amine with {2-chloro-9-[(1R,4S)-4-(di-Boc-amino)-cyclopent-2-enyl]-9H-purin-6-yl}-(2,2-diphenyl-ethyl)-amine.

Sources & evidence

ORD record
ord-21670e369c0f4128a3621c69817e3033
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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