1-Hexene → HCID 69538207, compound

HRID 2216271Notes

Reaction equation

HRID 2216271 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[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].[CH2:26]=[CH:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[CH:26](/[C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[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:27]\[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

3

Reactant 2

HCID 115971-HexeneHCID 86592815HCID 86592815, compound

Product 1

HCID 69538207HCID 69538207, compound

Procedure

The reaction was performed with 2-iodo-8-butylaminoadenosine (10, 380 mg, 0.82 mmol) and (E)-1-borocatechol)-1-hexene (2.46 mmol). The mixture was purified by column chromatography (10% MeOH in CH2Cl2). Yield 42 mg (0.10 mmol, 12%); Rƒ 0.44 (10% MeOH in CH2Cl2); 1H NMR (MeOD-d4) δ 6.94–6.80 (m, 1H, ═CHCH2), 6.28 (d, 1H, J=15.42 Hz, ═CH), 6.02 (d, 1H, J=7.62 Hz, H-1′), 4.81–4.69 (m, 1H, H-2′), 4.31–4.20 (m, 1H, H-3′), 4.20–4.05 (m, 1H, H-4′), 3.87–3.70 (m, 2H, H-5′), 3.35–3.23 (m, 2H, NHCH2), 2.29–2.05 (m, 2H, ═CHCH2), 1.72–1.20 (m, 8H, 2×CH2CH2), 1.00–0.83 (m, 6H, 2×CH3); MS m/z 422 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=8.53 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=20.47 min.

Workup

  1. customThe mixture was purified by column chromatography (10% MeOH in CH2Cl2)
  2. waitSystem B: 30–100% CH3OH in H2O in 40 min.

Sources & evidence

ORD record
ord-41ff308918ea41229f8e085dd3fefd0c
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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