Iodine → Triphenylphosphine Oxide

HRID 2264865ノート

反応式

HRID 2264865 の反応式
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:48]2[N:47]=[C:26]([NH:27]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[NH:25][C:23](=O)[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2].II.[CH:51]1[CH:56]=[CH:55][C:54]([P:57]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:53][CH:52]=1.[CH2:70]([C:73]1[NH:74][CH:75]=[CH:76][N:77]=1)[CH2:71][CH3:72].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O.O>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:20]=[N:21][C:22]2[C:48]1=[N:47][C:26]([NH2:27])=[N:25][C:23]=2[N:74]1[CH:75]=[CH:76][N:77]=[C:73]1[CH2:70][CH2:71][CH3:72])(=[O:3])[CH3:2].[P:57]([C:54]1[CH:53]=[CH:52][CH:51]=[CH:56][CH:55]=1)([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:3]

参加物

9

反応物 5

HCID 807IodineHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 1626172-PropylimidazoleHCID 1353995882',3',5'-tri-O-acetyl-2-N-tritylguanosine

生成物 2

HCID 13097Triphenylphosphine OxideHCID 687831079-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 22392675Trifluoroacetic acid water溶媒

反応条件

温度
95 °C

実験手順

A mixture of 2′,3′,5′-tri-O-acetyl-2-N-tritylguanosine (5.92 g, 9.1 mmol), I2 (11.55 g, 45.5 mmol), Ph3P (11.93 g, 45.5 mmol) and 2-propylimidazole (5.01 g, 45.5 mmol) was stirred in toluene (180 mL) at 95° C. for 15 min. DIPEA (15.9 mL, 11.80 g, 91.3 mmol) was added, and the mixture was stirred at 95° C. overnight. After removal of volatiles in vacuo, the residue was extracted with boiling EtOAc. The combined EtOAc extracts were evaporated to dryness, and the residue was dried under vacuum. The material obtained was stirred in TFA/H2O (9:1, 250 mL) at 0° C. for 4 h. Volatiles were evaporated in vacuo, and the residue was chromatographed (CH2Cl2→MeOH/CH2Cl2, 1:12). This solid material was treated with charcoal in MeOH. Volatiles were evaporated in vacuo, and the residue was dissolved in CH2Cl2 and washed (NaHCO3/H2O, brine) and dried (Na2SO4) to give 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine as a colored solid (3.20 g, 81%, contaminated with Ph3PO).

後処理

  1. customAfter removal of volatiles in vacuo
  2. extractionthe residue was extracted with boiling EtOAc
  3. customThe combined EtOAc extracts were evaporated to dryness
  4. customthe residue was dried under vacuum
  5. customThe material obtained
  6. customVolatiles were evaporated in vacuo
  7. customthe residue was chromatographed (CH2Cl2→MeOH/CH2Cl2, 1:12)
  8. additionThis solid material was treated with charcoal in MeOH
  9. customVolatiles were evaporated in vacuo
  10. dissolutionthe residue was dissolved in CH2Cl2
  11. washwashed (NaHCO3/H2O, brine)
  12. dry with materialdried (Na2SO4)

出典と根拠

ORDレコード
ord-6ca05d0b0b3b4eafa558b3583107b31e
出典データセット
uspto-grants-2010_12
特許番号
US07855285B2

反応ノート

読み込み中…