تفاعل #1596986

ord-2016b23188c84674be910a8f646abac6

معادلة التفاعل

C=CCn1c(=O)n([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)c2nc(N)ncc21
42
C=CCn1c(=O)n([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)c2nc(N)ncc21
7-Allyl-2-amino-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-7,9-dihydro-purin-8-one
O=C([O-])[O-].[K+].[K+]
K2CO3
C=CCn1c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2nc(N)ncc21
7-Allyl-2-amino-9-β-D-ribofuranosyl-7,9-dihydro-purin-8-one

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONTo the cloudy mixture was added Amberlite
  2. 2
    workup.STIRRING(0.5 g) and stirred till neutral and
  3. 3
    ترشيحfiltered
  4. 4
    تركيزThe filtrate was concentrated
  5. 5
    أخرىto give an off-white solid, which
  6. 6
    غسيلwas washed with water
  7. 7
    أخرىdried under high vacuum
  8. 8
    أخرىto give 93.5 mg of pure 43 in quantitative yield as an off white solid

الإجراء التجريبي

To a solution of 42 (0.13 g, 0.29 mmol) in methanol (4 mL) was added solid K2CO3 (0.024 g, 0.17 mmol) and the reaction stirred at ambient temperature for 18 h. To the cloudy mixture was added Amberlite CG-50 (0.5 g) and stirred till neutral and filtered. The filtrate was concentrated to give an off-white solid, which was washed with water and dried under high vacuum to give 93.5 mg of pure 43 in quantitative yield as an off white solid: 1H NMR (400 MHz, d6-DMSO) δ 7.88 (s, 1H), 6.33 (br s, 2H), 5.85 (m, 1H), 5.66 (d, J=6.0 Hz, 1H), 5.30 (d, J=5.6 Hz, 1H), 5.20 (s, 1H), 5.16 (d, J=8.4 Hz, 1H), 5.01 (d, J=4.8 Hz, 1H), 4.89 (q, J=5.6 Hz, 1H), 4.75 (br s, 1H), 4.35 (d, J=5.2 Hz, 2H), 4.10 (t, J=8.4 Hz, 1) 3.80 (q, J=3.6 Hz, 1H), 3.57 (m, 1H), 3.44 (m, 1H). MS (+)-ES [M+H]+ 324.1 m/z.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08211863B2uspto-grants-2012_07