Sodium Methoxide → 5'-O-acetyl-N-[(R)-1-(6ethoxy2-benzothiazolyl)thio-2-propyl]-2-chloroadenosine

HRID 375171Notes

Reaction equation

HRID 375171 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:44]2[N:43]=[C:42]([Cl:45])[N:41]=[C:23]([NH:24][C@H:25]([CH3:40])[CH2:26][S:27][C:28]3[S:29][C:30]4[CH:36]=[C:35]([O:37][CH2:38][CH3:39])[CH:34]=[CH:33][C:31]=4[N:32]=3)[C:22]=2[N:21]=[CH:20]1)(=O)C.C[O-].[Na+]>CO>[C:16]([O:15][CH2:14][C@H:8]1[O:7][C@@H:6]([N:19]2[C:44]3[N:43]=[C:42]([Cl:45])[N:41]=[C:23]([NH:24][C@H:25]([CH3:40])[CH2:26][S:27][C:28]4[S:29][C:30]5[CH:36]=[C:35]([O:37][CH2:38][CH3:39])[CH:34]=[CH:33][C:31]=5[N:32]=4)[C:22]=3[N:21]=[CH:20]2)[C@H:5]([OH:4])[C@@H:9]1[OH:10])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 228583072',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(6-ethoxy-2-benzothiazolyl)thio-2-propyl]adenosine

Product 1

HCID 228582965'-O-acetyl-N-[(R)-1-(6ethoxy2-benzothiazolyl)thio-2-propyl]-2-chloroadenosineYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Partial deacylation of the purified 2',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(6-ethoxy-2-benzothiazolyl)thio-2-propyl]adenosine (described in Example 19) using sodium methoxide in methanol provided the title 5'-O-acetyl-N-[(R)-1-(6ethoxy2-benzothiazolyl)thio-2-propyl]-2-chloroadenosine (0.070 g, 18%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.34-1.41 (6H, m, --CH2CH3 and --CHCH3), 2.03 (3H, s, --COCH3), 4.60 (1H, q, H-2'), 4.68 (1H, m, -CHCH3), 5.42, 5.62 (2H, 2d, 2'- and 3'-OH), 5.86 (1H, d, H-1'), 7.04 (1H, dd, Ar-H), 7.57, 7.72 (2H, 2d, Ar-H), 8.38 (1H, s, H-8), 8.52 (1H, d, N--H). HPLC retention time 25.6 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Sources & evidence

ORD record
ord-9a863d1c23aa4ad5a35afba8507e1d9f
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

Loading…