N-bromobutanimide → HCID 54109777, compound

HRID 1281679Notes

Reaction equation

HRID 1281679 reaction equation
[F:1][C:2]1[C:28]([F:29])=[CH:27][C:5]2[N:6]([C@@H:9]3[O:26][CH2:25][C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]3[O:11][C:12](=[O:14])[CH3:13])[CH:7]=[N:8][C:4]=2[CH:3]=1.[Br:30]N1C(=O)CCC1=O>O1CCCC1>[Br:30][C:7]1[N:6]([C@@H:9]2[O:26][CH2:25][C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[C:5]2[CH:27]=[C:28]([F:29])[C:2]([F:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54258191HCID 54258191, compound

Product 1

HCID 54109777HCID 54109777, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to General Procedure IV using 5,6-difluoro-1-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (1.1 g, 2.6 mmol), 60 ml tetrahydrofuran (Aldrich Sure Seal, Milwaukee), and a total of 2,8 g (16 mmol) of N-bromosuccinimide that was added in 3 ca. equivalent portions. The product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with hexanes and an increasing gradient from 5% to 20% ethyl acetate to give 1.0 g (2.0 mmol, 77% yield); MS (ES+): m/z (rel. intensity) 514 (1.0, M+23 (Na)); 1H NMR (DMSO-d6) δ8.26-8.21 (m, 1H), 7.73-7.69 (m, 1H), 5.93-5.91 (d, 1H, J=9.0 Hz), 5.69-5.62 (m, 3H), 4.11-3.90 (m, 2H), 2.20 (s, 3H), 1.98 (s,3H), 1.73 (s, 3H).

Workup

  1. customThe product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with hexanes
  2. customan increasing gradient from 5% to 20% ethyl acetate to give 1.0 g (2.0 mmol, 77% yield)

Sources & evidence

ORD record
ord-6ba5615b6f0c4844a5ee4651226b94ff
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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