Sodium Hydroxide → HCID 1284719, compound

HRID 1351116Notes

Reaction equation

HRID 1351116 reaction equation
[O:1]=C[C@@H]([C@@H]([C@@H](CO)O)O)O.O[C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH:13]1[C:22]#[C:23]C1N=C3C(NC=N3)=C(N)N=1)[CH2:19]2.OC12CC3CC(CC(C3)C1C#CC1N=C(N)C3N=CN(C=3N=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C2.[OH-].[Na+]>CO.Cl>[C:22]([C:13]1([OH:1])[CH:14]2[CH2:20][CH:18]3[CH2:17][CH:16]([CH2:21][CH:12]1[CH2:19]3)[CH2:15]2)#[CH:23]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5311110Aldehydo-D-riboseHCID 21097926HCID 21097926, compoundHCID 69323194HCID 69323194, compound

Product 1

HCID 1284719HCID 1284719, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Representative procedure for ribose cleavage: 2-{2-[hydroxy-adamantan-2-yl]ethyn-1-yl}adenine. A solution of 2-{2-[hydroxy-adamantan-2-yl]ethyn-1-yl}adenosine (3.486 g, 7.896 mmol) in methanol (100 mL) and 1.0 M HCl (10.0 mL) was stirred at 90° C. in a pressure apparatus for 18–50 h. The pH was adjusted to 4.2 with 5.0 M NaOH and the volume was reduced to half under reduced pressure. After cooling the resulting precipitate was filtered and washed with methanol to afford the pure product as a white solid: yield 2.153 g, 88%. 1H NMR (DMSO-d6) δ 8.13 (s, 1H), 7.25 (br s, 2H), 5.56 (s, 1H), 2.18–2.09, 1.94–1.89, 1.82–1.64, 1.52–1.45 (4×m, 12H). LRMS ESI (M+H+) 310.1.

Workup

  1. temperatureAfter cooling the resulting precipitate
  2. filtrationwas filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-6b907dda05b34371ba35c6ed87a0216f
Source dataset
uspto-grants-2007_05
Patent number
US07217702B2

Reaction notes

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