(1R,2S,3R,5S)-3-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diol → (1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol

HRID 215881Notes

Reaction equation

HRID 215881 reaction equation
FC(F)(F)C(O)=O.N[C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3NCC(C2C=CC=CC=2)C2C=CC=CC=2)[C@H](O)[C@@H]1O.ClC1N=C2C(N=CN2C2CC(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)C(O)C2O)=C(NCC(C2C=CC=CC=2)C2C=CC=CC=2)N=1.[Cl:88][C:89]1[N:97]=[C:96]2[C:92]([N:93]=[CH:94][N:95]2[C@@H:98]2[CH2:102][C@H:101]([N:103](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C@@H:100]([OH:118])[C@H:99]2[OH:119])=[C:91]([NH:120][C@H:121]([CH2:129][OH:130])[CH2:122][C:123]2[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=2)[N:90]=1>>[NH2:103][C@H:101]1[CH2:102][C@@H:98]([N:95]2[CH:94]=[N:93][C:92]3[C:96]2=[N:97][C:89]([Cl:88])=[N:90][C:91]=3[NH:120][C@H:121]([CH2:129][OH:130])[CH2:122][C:123]2[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=2)[C@H:99]([OH:119])[C@@H:100]1[OH:118]

Participants

4

Reactant 3

HCID 57777516(1R,2S,3R,5S)-3-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diolHCID 722787993-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diolHCID 86622631(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol trifluoroacetate

Product 1

HCID 86643676(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol

Procedure

(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol is prepared analogously to (1S,2R,3S,5R)-3-amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol trifluoroacetate (Step AAI3) by replacing 1R,2S,3R,5S)-3-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diol (Step AAI2) with (1R,2S,3R,5S)-3-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-5-(di-Boc-amino)-cyclopentane-1,2-diol (Step TA2).

Sources & evidence

ORD record
ord-dc20c91e99834f93a39678250a3a215e
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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