Sodium hydride → HCID 54170183, 화합물

HRID 611461

반응식

HRID 611461 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 54170183HCID 54170183, 화합물수율 28.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c768af7a0d224101ae34deeda17aa3c6
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001611

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