1-Hexene → HCID 69538204, compound

HRID 2216268Notes

Reaction equation

HRID 2216268 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:22])[C:5]2[N:6]=[C:7]([NH:20][CH3:21])[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH2:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH:23](/[C:2]1[N:3]=[C:4]([NH2:22])[C:5]2[N:6]=[C:7]([NH:20][CH3:21])[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])=[CH:24]\[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 115971-HexeneHCID 86592812HCID 86592812, compound

Product 1

HCID 69538204HCID 69538204, compound

Procedure

The reaction was performed with 2-iodo-8-methylaminoadenosine (7, 520 mg, 1.23 mmol) and (E)-1-borocatechol)-1-hexene (3.70 mmol). The mixture was purified by column chromatography (20% MeOH in CH2Cl2). Yield 42 mg (1.11 mmol, 9%), mp 161–166÷C; Rƒ 0.60 (20% MeOH in CH2Cl2); 1H NMR (MeOD-d4) δ 6.91–6.83 (m, 1H, ═CHCH2), 6.29 (d, 1H, J=15.44 Hz, ═CH), 5.98 (d, 1H, J=7.55 Hz, H-1′), 4.81–4.74 (m, 1H, H-2′), 4.29 (t, 1H, J=5.49 Hz, H-3′), 4.13 (m, 1H, H-4′), 3.82–3.79 (m, 2H, H-5′), 2.97 (m, 3H, NHCH3), 2.29–2.22 (m, 2H, ═CHCH2), 1.52–1.36 (m, 4H, CH2CH2), 0.94 (t, 3H, J=6.52 Hz, CH3); MS m/z 379 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=6.15 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=18.67 min.

Workup

  1. customThe mixture was purified by column chromatography (20% MeOH in CH2Cl2)
  2. waitSystem B: 30–100% CH3OH in H2O in 40 min.

Sources & evidence

ORD record
ord-7f8e2e67ca5d4f84b8d68a4a56bf2fbf
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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