Sodium Bicarbonate → HCID 10409480, compound

HRID 1708107Notes

Reaction equation

HRID 1708107 reaction equation
C([NH:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[CH2:14][CH:15]([CH2:28][O:29][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)/[CH:16]=[CH:17]/[P:18]([O:24][CH:25]([CH3:27])[CH3:26])([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[C:7](Cl)[N:6]=1)(=O)C.[C:48](=O)(O)[O-:49].[Na+]>Cl>[NH2:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[CH2:14][CH:15]([CH2:28][OH:29])/[CH:16]=[CH:17]/[P:18]([O:20][CH:21]([CH3:23])[CH3:22])([O:24][CH:25]([CH3:27])[CH3:26])=[O:19])=[C:7]([O:49][CH3:48])[N:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 10394959HCID 10394959, compound

Product 1

HCID 10409480HCID 10409480, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (E)-2-acetamido-9-[2-(t-butyldiphenylsilyloxy)methyl-4-(diisopropoxyphosphoryl)but-3-enyl]-6-chloropurine (330 mg, 473 μmol) in 7% methanolic hydrogen chloride (15 ml) was stirred at room temperature for 7 h. The solution was reduced to 1/3 volume then neutralised by addition of saturated sodium bicarbonate solution. The solvent was removed and the residue purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1, 6:1) to give (E)-2-amino-9-[4-(diisopropoxyphosphoryl)-2-(hydroxymethyl)but-3-enyl]-6-methoxypurine as a colourless gum (140 mg, 72%); λmax (EtOH) 249 (8,632) and 283 (9,086)nm; υmax (KBr) 3335, 2980, 1610, 1585, 1475, 1410, 1400 and 1250 cm-1 ; δH [(CD2)2SO] 1.10 (12H, m, CH(CH3)2), 3.02 (1H, m, CH), 3.50 (2H, t, J 5 Hz, CH2O), 3.94 (3H, s, CH3O), 4.10-4.40 (4H, m, CH2N and CH(CH3)2), 4.97 (1H, t, J 5 Hz, D2O exchangeable, OH), 5.61 (1H, dd, J 17 Hz and 20 Hz, PCH=CH), 6.43 (2H, br.s, D2O exchangeable, NH2), 6.50 (1H, ddd, J 8 Hz, 17 Hz and 22 Hz, PCH=CH), 7.80 (1H, s, H-8) (Found: MH+ 414. 1900). C17H28N5O5P requires MH+ 414.1906).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1, 6:1)

Sources & evidence

ORD record
ord-c4fbc595f90a41c5ad9ccd2efbbef6eb
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Reaction notes

Loading…