DL-alpha-Tocopherol → Isopropylidene-5-bromouridine

HRID 1252266

반응식

HRID 1252266 반응식
[CH3:1][C:2]1C(C)=C2C(CCC(CCCC(CCCC(CCCC(C)C)C)C)(C)O2)=C(C)[C:3]=1O.P(Cl)(Cl)(Cl)=O.[Br:37][C:38]1[C:39](=[O:54])[NH:40][C:41](=[O:53])[N:42]([CH:52]=1)[C@@H:43]1[O:51][C@H:48]([CH2:49][OH:50])[C@@H:46]([OH:47])[C@H:44]1[OH:45].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.N1C=CC=CC=1.C1C=CC=CC=1>[C:2](=[C:49]([OH:50])[C@H:48]1[O:51][C@@H:43]([N:42]2[CH:52]=[C:38]([Br:37])[C:39](=[O:54])[NH:40][C:41]2=[O:53])[C@H:44]([OH:45])[C@@H:46]1[OH:47])([CH3:3])[CH3:1]

참가 물질

8

반응물 4

HCID 2116DL-alpha-TocopherolHCID 6101p-Toluenesulfonic acidHCID 24813Phosphorus oxychlorideHCID 914945-Bromouridine

생성물 1

HCID 67931710Isopropylidene-5-bromouridine

시약·촉매·용매 3

HCID 180Acetone용매HCID 241Benzene용매HCID 1049Pyridine용매2회

실험 절차

The phosphrylation reaction described in Example 1 is repeated except that 4.3 g (0.01 mol) of DL-alpha-tocopherol, 4 g of pyridine, 3.06 g of phosphorus oxychloride, and 50 ml of benzene are used. Separately, 5-bromouridine is treated with p-toluene-sulfonic acid in aceton to give isopropylidene-5-bromouridine and 4.35 g (0.012 mol) of this isopropylidene-5-bromouridine and 2 g of pyridine are dissolved in 60 ml of tetrahydrofuran. Then, the reaction and workup procedures of Example 1 are followed to give the potassium salt and, then, the free acid. The free acid is recrystallized from ethanol to give 2.5 g of colorless crystals melting at 177°-178° C.

후처리

  1. customThe phosphrylation reaction

출처 및 근거

ORD 기록
ord-65eadf7818c243e69ef7911104a904e9
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04742163

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