Diisopropylethylamine → N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2'-deoxyadenosine

HRID 1811373노트

반응식

HRID 1811373 반응식
[C@@H:1]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13](O)[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C(N(CC)C(C)C)(C)C.[I:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([NH2:37])[CH3:36])=[C:31]([N+:38]([O-:40])=[O:39])[CH:30]=1>CN(C=O)C>[I:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([NH:37][C:13]2[C:12]3[N:11]=[CH:10][N:9]([C:18]=3[N:17]=[CH:16][N:15]=2)[C@@H:1]2[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)[CH3:36])=[C:31]([N+:38]([O-:40])=[O:39])[CH:30]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 668309681-(4-Iodo-2-nitrophenyl)ethylamineHCID 178521064HCID 178521064, 화합물

생성물 1

HCID 86620496N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2'-deoxyadenosine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of 2′-deoxyinosine (150 mg, 0.6 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphonate (BOP, 379 mg, 0.86 mmol) in anhydrous DMF (1.5 mL), N,N-diisopropylethylamine (186 μL, 1.1 mmol) was added followed by the addition of a solution of 1-(4-iodo-2-nitrophenyl)ethylamine (460 mg, 1.57 mmol) in anhydrous DMF (0.5 mL). The mixture was stirred under nitrogen atmosphere for 48 hours. DMF was removed in vacuo, and the crude product was purified by silica gel column chromatography to yield N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2′-deoxyadenosine dA.20 (204 mg, 65%, 1:1 mixture of diastereomers) as a white foam.

후처리

  1. additionwas added
  2. customDMF was removed in vacuo
  3. customthe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-af78824316ed43cfa8e904e645a55f9f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08361727B2

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