Water → HCID 178482043, compound

HRID 53473Notes

Reaction equation

HRID 53473 reaction equation
[CH3:1][NH:2][C:3]1[C:4]2[N:5]=[CH:6][N:7]([C:17]=2[N:18]=[CH:19][N:20]=1)[C@@H:8]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[C@H:9]1[OH:10].ClC1C=CC=C(C(OO)=[O:29])C=1.O>C(O)(=O)C>[CH3:1][NH:2][C:3]1[N+:20]([O-:29])=[CH:19][N:18]=[C:17]2[C:4]=1[N:5]=[CH:6][N:7]2[C@@H:8]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[C@H:9]1[OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 102175N6-Methyladenosine

Product 1

HCID 178482043HCID 178482043, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N6 -methyladenosine (2 g, 6.7 mmol) and m-chloroperbenzoic acid (2.3 g, 13.4 mmol) in acetic acid (20 ml) was stirred at room temperature for two days. Water (20 ml) was added to the reaction mixture, and a resulting thick precipitate was removed by filtration and discarded. The filtrate was co-evaporated repeatedly with water under high vacuum, and the foamy residue was chromatographed on a silica gel column (CHCl3 : MeOH 2:1). The product was obtained as a white solid (mp 145° C., crystallization from EtOH) in 45% yield (0.9 g). 1H NMR (DMSO)d: 8.62 (s, H-2), 8.55 (s, H-8), 5.88 (d, J=5.4 Hz, 1H, H-1), 4.51 (`t`, J=5.1 Hz, 1H, H-2'), 4.15 (`t`, J=4.5 Hz, 1H, H-3'), 3.94 (ABq, 1H, H-4'), 3.61 (ABdq, J=12, 4 Hz, 2H, H-5'), 3.46 (s, 3H, Me) ppm. MS (CI) m/e: 298 (MH+).

Workup

  1. customa resulting thick precipitate was removed by filtration
  2. customthe foamy residue was chromatographed on a silica gel column (CHCl3 : MeOH 2:1)
  3. customThe product was obtained as a white solid (mp 145° C., crystallization from EtOH) in 45% yield (0.9 g)

Sources & evidence

ORD record
ord-f53c5f46d7774a619f38bdbfe67dd200
Source dataset
uspto-grants-1997_04
Patent number
US05620676

Reaction notes

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