HCID 86663292, compound → HCID 86663291, compound

HRID 529276Notes

Reaction equation

HRID 529276 reaction equation
[N:1]([C@:4]1([CH2:36][O:37]C(=O)C2C=CC=CC=2)[O:8][C@@:7]([CH3:17])([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[C@:6](C(=O)C2C=CC=CC=2)([OH:18])[C@:5]1(C(=O)C1C=CC=CC=1)[OH:27])=[N+:2]=[N-:3]>N>[N:1]([C@:4]1([CH2:36][OH:37])[O:8][C@@:7]([CH3:17])([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[C@H:6]([OH:18])[C@@H:5]1[OH:27])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 86663292HCID 86663292, compound

Product 1

HCID 86663291HCID 86663291, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

4′-Azido-1′-methyl-2′,3′,5′-O-tribenzoyluridine (37-7) (0.20 g, 0.34 mmol) was dissolved in saturated methanolic ammonia (50 mL), and the mixture was stirred at R.T. for 14 hours. The solvent was removed, and the residue was purified on a silica gel column (DCM/MeOH=50:1 to 30:1) to give (54) as a white solid (47 mg, 46.0%). 1H NMR (CD3OD, 400 MHz) δ 8.15 (d, J=8.4 Hz, 1H), 5.63 (d, J=8.4 Hz, 1H), 4.73 (d, J=5.6 Hz, 1H), 4.17 (d, J=5.2 Hz, 1H), 3.67 (d, J=12.0 Hz, 1H), 3.55 (d, J=12.0 Hz, 1H), 1.76 (s, 3H); ESI-negative-MS: m/z=298.1 [M−H]+, 597.2 [2M+H]+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on a silica gel column (DCM/MeOH=50:1 to 30:1)

Sources & evidence

ORD record
ord-13a88f50652f4205811af84cd206848f
Source dataset
uspto-grants-2016_05
Patent number
US09346848B2

Reaction notes

Loading…