2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → cis-N-[2-[(2-benzothiazolyl)thio]cyclopentyl]-2-chloroadenosine

HRID 375158Notes

Reaction equation

HRID 375158 reaction equation
Cl.S1C2C=CC=CC=2N=C1[C@H]1CCC[C@H]1N.C(O[C@@H]1[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1N1C=NC2C1=NC(Cl)=NC=2Cl)(=O)C.C([O:49][C@@H:50]1[C@H:54]([O:55]C(=O)C)[C@@H:53]([CH2:59][O:60]C(=O)C)[O:52][C@H:51]1[N:64]1[C:88]2[N:87]=[C:86]([Cl:89])[N:85]=[C:68]([NH:69][C@@H:70]3[CH2:74][CH2:73][CH2:72][C@@H:71]3[S:75][C:76]3[S:77][C:78]4[CH:84]=[CH:83][CH:82]=[CH:81][C:79]=4[N:80]=3)[C:67]=2[N:66]=[CH:65]1)(=O)C.C[O-].[Na+]>CO.C(N(CC)CC)C>[S:77]1[C:78]2[CH:84]=[CH:83][CH:82]=[CH:81][C:79]=2[N:80]=[C:76]1[S:75][C@H:71]1[CH2:72][CH2:73][CH2:74][C@H:70]1[NH:69][C:68]1[C:67]2[N:66]=[CH:65][N:64]([C:88]=2[N:87]=[C:86]([Cl:89])[N:85]=1)[C@@H:51]1[O:52][C@H:53]([CH2:59][OH:60])[C@@H:54]([OH:55])[C@H:50]1[OH:49]

Participants

7

Reactant 4

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 10942334Sodium MethoxideHCID 22858330cis-2',3',5'-tri-O-acetyl-N-[2-[(2-benzothiazolyl)thio]cyclopentyl]-2-chloroadenosineHCID 67722584cis-2-(2-Benzothiazolyl)cyclopentylamine hydrochloride

Product 1

HCID 54248568cis-N-[2-[(2-benzothiazolyl)thio]cyclopentyl]-2-chloroadenosineYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

The above cis-2-(2-benzothiazolyl)cyclopentylamine hydrochloride (1.5 g, 4.6 mmol) was combined with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 4.5 mmol) and triethylamine (2.49 ml) and reacted by the method described in Example 1. Deacylation of the purified cis-2',3',5'-tri-O-acetyl-N-[2-[(2-benzothiazolyl)thio ]cyclopentyl]-2-chloroadenosine using sodium methoxide in methanol provided the title cis-N-[2-[(2-benzothiazolyl)thio]cyclopentyl]-2-chloroadenosine (0.89 g, 38%) as a foam (following column chromatography) (a ca. 2:1 mixture of diastereoisomers), 1H NMR (DMSO-d6) δ 1.62-2.45 (6H, 5m, --CH2CH2CH2 --), 3.52-3.60 (1H, m, H-5'a), 3.64-3.70 (1H, m, H-5'b), 3.94 (1H, br q, H-4'), 4.11 (1H, br q, H-3'), 4.62 (1H, q, H-2'), 5.75-5.83 (1H, 2m, H-1'), 7.26-7.94 (4H, 4m, Ar-H).

Workup

  1. customreacted by the method

Sources & evidence

ORD record
ord-90a9d367870443e6aaa39b889d0cbbca
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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