Sodium hydride → HCID 54170183、化合物

HRID 611461

反応式

HRID 611461 の反応式
[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:46]=2[N:47]=[CH:48][N:49]=1)[C@@H:15]1[O:45][C@H:19]([CH2:20][O:21][C:22]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:52]([C:56]1[CH:63]=[CH:62][C:59]([CH2:60]Br)=[CH:58][CH:57]=1)([CH3:55])([CH3:54])[CH3:53]>CN(C=O)C>[C:1]([N:9]([CH2:60][C:59]1[CH:62]=[CH:63][C:56]([C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:57][CH:58]=1)[C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:46]=2[N:47]=[CH:48][N:49]=1)[C@@H:15]1[O:45][C@H:19]([CH2:20][O:21][C:22]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C@@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 2724489Adenosine, N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxy-

生成物 1

HCID 54170183HCID 54170183、化合物収率 28.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To N6 -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (658 mg, 1.0 mmole) was added DMF (anhydrous, 10 ml) and evaporated to dryness. This was repeated. Fresh DMF (10 ml) was added under an Argon atmosphere. Sodium hydride (44 mg, 60% in oil, 1.1 mmole) was added and the mixture was stirred for 0.5 hour at room temperature. 4-(tert-butyl)benzyl bromide (272 mg, 1.2 mmole) was added dropwise and stirred at room temperature overnight. The solvent was removed under vacuum, and the residue was partitioned between ethyl acetate and water (20 ml each). The organic phase was washed with water (3 times, 20 ml), dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude product was purified by column chromatography on silica gel (100 g), using methylene chloride:methanol:triethylamine 96.5:3:0.5 to yield N -benzoyl-N -(p-tert-butylbenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine, (229 mg, 28.5%).

後処理

  1. customevaporated to dryness
  2. additionFresh DMF (10 ml) was added under an Argon atmosphere
  3. stirringstirred at room temperature overnight
  4. customThe solvent was removed under vacuum
  5. customthe residue was partitioned between ethyl acetate and water (20 ml each)
  6. washThe organic phase was washed with water (3 times, 20 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crude product was purified by column chromatography on silica gel (100 g)

出典と根拠

ORDレコード
ord-c768af7a0d224101ae34deeda17aa3c6
出典データセット
uspto-grants-1999_12
特許番号
US06001611

関連ノート

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