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Ethanol → Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethanesulfonate

HRID 552708
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인쇄 미리보기

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HRID 552708 반응식
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH:21]=[CH:22][S:23]([O:26][CH2:27][CH3:28])(=[O:25])=[O:24])[O:12]1.C(O)C.[BH4-].[Na+]>O.[Cl-].[NH4+]>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:19])([CH3:20])[O:18][C@@H:14]2[C@@H:13]([CH2:21][CH2:22][S:23]([O:26][CH2:27][CH3:28])(=[O:24])=[O:25])[O:12]1
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참가 물질

6

반응물 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86607308Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethenesulfonate

생성물 1

HCID 86607309Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethanesulfonate수율 93.2%

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 25517Ammonium Chloride용매

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온도
25 °C

실험 절차

Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethenesulfonate (10.500 g, 0.024370 mol) was dissolved in ethanol (200 mL, 3 mol) in a 1-necked round-bottom flask. Sodium borohydride (507.1 mg, 0.01340 mol) was added in 2 portions, 10 min apart. The reaction was stirred for a further 15 min at 25° C. The reaction was diluted with water (400 mL) and 5M ammonium chloride in water (50 mL) and was concentrated in vacuo to remove most of the ethanol. The aqueous residue was extracted with methylene chloride (2×250 mL) and the organic phase was concentrated in vacuo to yield crude product (9.83 g).

후처리

  1. concentrationwas concentrated in vacuo
  2. customto remove most of the ethanol
  3. extractionThe aqueous residue was extracted with methylene chloride (2×250 mL)
  4. concentrationthe organic phase was concentrated in vacuo

출처 및 근거

ORD 기록
ord-b14f3b50a4ce422d9bd03c406fb043e7
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951810B2

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