Adenine → 9-(2-Hydroxypropyl)adenine, (R)-

HRID 1716371

反応式

HRID 1716371 の反応式
N1C(N)=C2C(N=CN2)=NC=1.[CH3:11][C@@H:12]([O:24]CP(O)(O)=O)[CH2:13][N:14]1[C:18]2[N:19]=[CH:20][N:21]=[C:22]([NH2:23])[C:17]=2[N:16]=[CH:15]1.CC(C)([O-])C.[Mg+2].CC(C)([O-])C.C1(=O)O[C@H](C)CO1.CS(O)(=O)=O>CN(C=O)C.[OH-].[Na+].C1(C)C=CC=CC=1>[OH:24][C@H:12]([CH3:11])[CH2:13][N:14]1[CH:15]=[N:16][C:17]2[C:18]1=[N:19][CH:20]=[N:21][C:22]=2[NH2:23]

参加物

9

反応物 5

HCID 190Adenine2 回HCID 6395Methanesulfonic AcidHCID 464205TenofovirHCID 641813(4R)-4-methyl-1,3-dioxolan-2-oneHCID 12040442Magnesium 2-methylpropan-2-olate

生成物 1

HCID 4452119-(2-Hydroxypropyl)adenine, (R)-収率 75%

試薬・触媒・溶媒 3

HCID 14798Sodium Hydroxide触媒HCID 1140Toluene溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Adenine to PMPA using Magnesium t-Butoxide. To a suspension of adenine (40 g, 0.296 mol) in DMF (41.9 ml) was added (R)-propylene carbonate (34.5 g, 0.338 mol) and sodium hydroxide (0.480 g, 0.012 mol). The mixture was heated at 130° C. overnight. The reaction was cooled to 100° C. and toluene (138 ml) was added followed by methanesulfonic acid (4.7 g, 0.049 mol) while maintaining the reaction temperature between 100-110° C. Additional toluene (114 ml) was added to create a homogeneous solution. The solution was cooled to 3° C. over 7 hours and then held at 3° C. for one hour. The resulting solid was isolated by filtration and rinsed with acetone (2×). The wet solid was dried in vacuo at 80° C. to yield 42.6 g (75%) of (R)-9-[2-(hydroxy)propyl]adenine (HPA) as an off-white solid. Mp: 188-190° C.

後処理

  1. temperatureThe reaction was cooled to 100° C.
  2. temperaturewhile maintaining the reaction temperature between 100-110° C
  3. temperatureThe solution was cooled to 3° C. over 7 hours
  4. customThe resulting solid was isolated by filtration
  5. washrinsed with acetone (2×)
  6. customThe wet solid was dried in vacuo at 80° C.

出典と根拠

ORDレコード
ord-887f2502f2ad4e9f9769df6dc5736a14
出典データセット
uspto-grants-2010_09
特許番号
US07803788B2

関連ノート

読み込み中…