2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → N-[(R)-1-(2-benzothiazolyl)thio-2-butyl]-2-chloroadenosine

HRID 375156Notes

Reaction equation

HRID 375156 reaction equation
Cl.[NH2:2][C@H:3]([CH2:15][CH3:16])[CH2:4][S:5][C:6]1[S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.C([O:20][C@@H:21]1[C@H:25]([O:26]C(=O)C)[C@@H:24]([CH2:30][O:31]C(=O)C)[O:23][C@H:22]1[N:35]1[CH:43]=[N:42][C:41]2[C:36]1=[N:37][C:38]([Cl:45])=[N:39][C:40]=2Cl)(=O)C.C(O[C@@H]1[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1N1C2N=C(Cl)N=C(N[C@H](C)CSC3SC4C=CC=CC=4N=3)C=2N=C1)(=O)C.C[O-].[Na+]>CO>[S:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[S:5][CH2:4][C@H:3]([NH:2][C:40]1[C:41]2[N:42]=[CH:43][N:35]([C:36]=2[N:37]=[C:38]([Cl:45])[N:39]=1)[C@@H:22]1[O:23][C@H:24]([CH2:30][OH:31])[C@@H:25]([OH:26])[C@H:21]1[OH:20])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 10942334Sodium MethoxideHCID 228583012',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosineHCID 677714892-[(R)-2-amino-1-butylthio]benzothiazole hydrochloride

Product 1

HCID 22858288N-[(R)-1-(2-benzothiazolyl)thio-2-butyl]-2-chloroadenosineYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to general method A as described above in Example 1 by reacting 2-[(R)-2-amino-1-butylthio]benzothiazole hydrochloride (1.16 g, 4.2 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.57 g, 3.5 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine using sodium methoxide in methanol. This provided the title N-[(R)-1-(2-benzothiazolyl)thio-2-butyl]-2-chloroadenosine (0.93 g, 51%) (following column chromatography), 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CH2CH3), 1.65-1.86 (2H, m, --CH2CH3), 3.95 (1H, q, H-4'), 4.14 (1H, d, H-3'), 4.48-4.62 (2H, m, H-2' and --CHCH2H3), 5.07 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 7.34, 7.45 (2H, 2t, Ar-H), 7.84, 8.0 (2H, 2d, Ar-H). HPLC retention time 21.8 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-1c70d6e901ec4d3389de346f63a0d3aa
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

Loading…