Sodium Hydroxide → 2-(5-Hexenylthio)adenosine hemihydrate

HRID 53474

반응식

HRID 53474 반응식
[CH:1]1[N:10]([C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])[C:9]2[C:3](=[C:4]([NH2:20])[NH:5][C:6]([N:8]=2)=[S:7])[N:2]=1.[OH-].[Na+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH2:29]>>[OH2:15].[CH2:29]([S:7][C:6]1[N:5]=[C:4]([NH2:20])[C:3]2[N:2]=[CH:1][N:10]([C:9]=2[N:8]=1)[C@@H:11]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]1[OH:19])[CH2:28][CH2:27][CH2:26][CH:25]=[CH2:24].[CH2:29]([S:7][C:6]1[N:5]=[C:4]([NH2:20])[C:3]2[N:2]=[CH:1][N:10]([C:9]=2[N:8]=1)[C@@H:11]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]1[OH:19])[CH2:28][CH2:27][CH2:26][CH:25]=[CH2:24]

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 759066-Bromo-1-hexeneHCID 64519652-Thioadenosine

생성물 1

HCID 677111252-(5-Hexenylthio)adenosine hemihydrate수율 55%

실험 절차

2-Thioadenosine (0.2 g, 0.67 mmol) was dissolved in 0.25M NaOH (8 ml, 2 mmol). 6-Bromo-1-hexene (0.45 ml, 3.3 mmol) was added, and the solution was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure (bath temp. 33° C.) and extracted with ether (2×2 ml). The aqueous phase was neutralized with 18% HCl and extracted with ethyl acetate (3×4 ml). The homogeneous product was obtained after drying and solvent removal as a yellowish solid (0.14 g, 55% yield, mp 94° C., trituration with ether). 1H NMR (CD3OD)d: 8.16 (s, 1H, H-8), 5.91 (d, J=5.8 Hz, 1H, H-1'), 5.8 (dm, 1H, olefinic), 4.93 (ddd, J=11, 9.7, 1 Hz, 2H, olefinic), 4.72 (`t`, 1H, J=5 Hz H-2'), 4.31 (m, 1H, H-3'), 4.11 (m, 1H, H-4'), 3.83 (m, 2H, H-5'), 3.16 (m, 2H, CH2S), 2.10 (m, 2H, CH2), 1.74 (m, 2H, CH2), 1.56 (m, 2H, CH2) ppm. Anal. calc. for C16H23N5O4S.0.5H2O: C, 49.22; H, 6.20; N, 17.93. Found: C, 49.46; H, 5.99; N, 17.36.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure (bath temp. 33° C.)
  2. extractionextracted with ether (2×2 ml)
  3. extractionextracted with ethyl acetate (3×4 ml)
  4. customThe homogeneous product was obtained
  5. customafter drying
  6. customsolvent removal as a yellowish solid (0.14 g, 55% yield, mp 94° C., trituration with ether)

출처 및 근거

ORD 기록
ord-5a6a6dff933a4d7bb05e4e1f68e8b190
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620676

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