Phthalimide → HCID 69420144、化合物

HRID 1374072

反応式

HRID 1374072 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[C:31]([NH:39][C:40]1[C:41]2[N:42]=[CH:43][N:44]([C:53]=2[N:54]=[CH:55][N:56]=1)[C@@H:45]1[O:52][C@H:49]([CH2:50][OH:51])[C@@H:47]([OH:48])[CH2:46]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:20]1(=[O:30])[N:24]([CH:50]([OH:51])[C@H:49]2[O:52][C@@H:45]([N:44]3[C:53]4[N:54]=[CH:55][N:56]=[C:40]([NH:39][C:31](=[O:38])[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[C:41]=4[N:42]=[CH:43]3)[CH2:46][C@@H:47]2[OH:48])[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 107558N-benzoyl-2'-deoxyadenosine

生成物 1

HCID 69420144HCID 69420144、化合物収率 29.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

13.11 g (50 mmol) triphenylphosphine, 6.99 g (47.5 mmol) phthalimide and 17.77 g (50 mmol) N6-benzoyl-2′-deoxyadenosine were stirred in 400 mL dry THF, and added 9.84 mL (50 mmol) of diisopropyl azodicarboxylate under a nitrogen atmosphere. After stirring in an ice-water bath for 2 h and at the ambient temperature for 4 h, the reaction mixture was concentrated and the residue was added 100 mL dichloromethane. The precipitates thus formed were removed by filtration and the filtrate was concentrated and flashed through a silica gel column with 2:1 dichloromethane-THF and 19:1 dichloromethane-methanol to give 7.1 g of 5′-phthalimido-N6-benzoyl-2′-deoxyadenosine.

後処理

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue was added 100 mL dichloromethane
  3. customThe precipitates thus
  4. customformed
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-f641fc51dfce4851aeafac4cc703fe78
出典データセット
uspto-grants-2007_01
特許番号
US07164014B2

関連ノート

読み込み中…