Sodium Methoxide → 5'-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3yl)]thio-2-propyl}adenosine

HRID 375172Notes

Reaction equation

HRID 375172 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:43]2[N:42]=[C:41]([Cl:44])[N:40]=[C:23]([NH:24][C@H:25]([CH3:39])[CH2:26][S:27][C:28]3[N:32]=[C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[NH:30][N:29]=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:43]3[N:42]=[C:41]([Cl:44])[N:40]=[C:23]([NH:24][C@H:25]([CH3:39])[CH2:26][S:27][C:28]4[N:32]=[C:31]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[NH:30][N:29]=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 22858306HCID 22858306, compound

Product 1

HCID 228582835'-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3yl)]thio-2-propyl}adenosineYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Partial deacylation of the purified 2',3',5'-Tri-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3-yl)]thio-2-propyl}adenosine (described in Example 27) using sodium methoxide in methanol to provide the title 5'-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3yl) ]thio-2-propyl}-adenosine (0.035 g, 8%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ 1.34 (3H, d, --CHCH3), 2.02 (3H, s, --COCH3), 4.53-4.68 (2H, q, H-2' and --CHCH3), 5.40, 5.61 (2H, 2d, 2'- and 3'-OH), 5.86 (1H, d, H-1'), 7.38-8.01 (5H, 3m, Ar-H), 8.37 (1H, s, H-2). HPLC retention time 16.9 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Sources & evidence

ORD record
ord-b47b3e22d05642cbaf4f76a5ca85e02b
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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