Hydrochloric Acid → HCID 22858287, compound

HRID 2292620Notes

Reaction equation

HRID 2292620 reaction equation
C(OC(N[C@H](C)CS(C1SC2C=CC=CC=2N=1)(=O)=O)=O)(C)(C)C.Cl.Cl.NC(C)C[C@H](S(C1SC2C=CC=CC=2N=1)(=O)=O)CC.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:77][C@@H:78]1[C@H:82]([O:83]C(=O)C)[C@@H:81]([CH2:87][O:88]C(=O)C)[O:80][C@H:79]1[N:92]1[C:116]2[N:115]=[C:114]([Cl:117])[N:113]=[C:96]([NH:97][C@H:98]([CH3:112])[CH2:99][S:100]([C:103]3[S:104][C:105]4[CH:111]=[CH:110][CH:109]=[CH:108][C:106]=4[N:107]=3)(=[O:102])=[O:101])[C:95]=2[N:94]=[CH:93]1)(=O)C.C[O-].[Na+]>C(OCC)(=O)C.CO>[S:104]1[C:105]2[CH:111]=[CH:110][CH:109]=[CH:108][C:106]=2[N:107]=[C:103]1[S:100]([CH2:99][C@H:98]([NH:97][C:96]1[C:95]2[N:94]=[CH:93][N:92]([C:116]=2[N:115]=[C:114]([Cl:117])[N:113]=1)[C@@H:79]1[O:80][C@H:81]([CH2:87][OH:88])[C@@H:82]([OH:83])[C@H:78]1[OH:77])[CH3:112])(=[O:101])=[O:102]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 10942334Sodium MethoxideHCID 22858311HCID 22858311, compoundHCID 54348390HCID 54348390, compoundHCID 67771484HCID 67771484, compound

Product 1

HCID 22858287HCID 22858287, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[(R)-2-(N-tert-Butyloxycarbonylamino)-1-propylsulphonyl]benzothiazole was prepared by oxidation of 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylthio]benzothiazole (see Example 5) (0.55 g, 1.7 mmol) with "Oxone" on a Montmorillionite support. A mixture of the sulphonyl and sulphinyl derivatives was obtained, and the 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylsulphonyl]benzothiazole was isolated following column chromatography. Deprotection was performed under standard conditions with hydrogen chloride in ethyl acetate. The resultant 2-[(R)-2-aminopropyl-1-propylsulphonyl]benzothiazole hydrochloride (0.088 g, 0.4 mmol) was reacted with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (0.18 g, 0.4 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(2-benzothiazolyl)sulphonyl-2-propyl]-2-chloroadenosine using sodium methoxide in methanol provided the title N-[(R)-1-(2-benzothiazolyl)sulphonyl-2-propyl]-2-chloroadenosine as a foam (following column chromatography); 1H NMR (DMSO-d6) δ1.83 (3H, d, --CHCH3), 3.55, 3.66 (2H, ABX, H-5'a and H-5'b), 3.96 (1H, q, H-4'), 4.17 (1H, q, H-3'), 4.59 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.24, 5.68 (2H, 2d, 2'- and 3'-OH), 5.95 (1H, d, H-1'), 7.34, 7.47 (2H, 2t, Ar--H), 7.84, 8.01 (2H, 2d, Ar--H), 8.14 (1H, t, N--H), 8.71 (1H, s, H-8). HPLC retention time 13.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Sources & evidence

ORD record
ord-0c5e082805c94dc4851d4e11cd2ce560
Source dataset
uspto-grants-1997_11
Patent number
US05683989

Reaction notes

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