Dimethylformamide → HCID 178486368, compound

HRID 915879Notes

Reaction equation

HRID 915879 reaction equation
[CH3:1][C@@:2]1([OH:24])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:23]=[C:14]2[CH:15]=[CH:16][C:17]3[C:18](=[O:22])[NH:19][N:20]=[CH:21][C:12]([C:13]=32)=[N:11]1.[Br:25]N1C(=O)CCC1=O.CN([CH:36]=[O:37])C>>[CH3:1][C@@:2]1([OH:24])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:23]=[C:14]2[CH:15]([O:37][CH3:36])[CH:16]([Br:25])[C:17]3[C:18](=[O:22])[NH:19][N:20]=[CH:21][C:12]([C:13]=32)=[N:11]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 86612905HCID 86612905, compound

Product 1

HCID 178486368HCID 178486368, compound

Conditions

Temperature
0 °C

Procedure

To a stirred solution of nucleoside 6.6 (10 mg, 0.030 mmol) in DMF (0.5 mL) was added N-bromosuccinimide (11.25 mg, 2.10 eq.) at 0° C. under argon. The reaction mixture was stirred at 0° C. for 1 hr then quenched with MeOH (0.5 mL). The mixture was evaporated to dryness and the residue was purified on a silica gel column with 5% MeOH in CH2Cl2 to give compound 14.1 as a mixture of diastereoisomers (8 mg, 65%). The isolated compound was characterized by 1H NMR, COSY, NOESY and LCMS. 1H NMR (300 MHz, DMSO-d6) δ 11.29 (s, 1H, NH), 8.54 (s, 1H, H-4), 8.00 (s, 1H, H-1), 6.24, 6.21 (2s, 1H, H-1′), 5.22-5.08 (m, 4H, 3×OH, H-8), 4.77-4.73 (m, 1H, H-9), 3.95-3.7 (m, 4H, H-3′, H-4′ 2×H-5′), 3.24, 3.21 (2s, 3H, OCH3), 0.68, 0.66 (2s, 3H, CH3). ES MS: 501.7 (M+CH3COO−).

Workup

  1. customthen quenched with MeOH (0.5 mL)
  2. customThe mixture was evaporated to dryness
  3. customthe residue was purified on a silica gel column with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-dad3bf98aa4146ffb9dde013e227daf3
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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