Lithium azide → HCID 10017261, compound

HRID 649747Notes

Reaction equation

HRID 649747 reaction equation
[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3Cl)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[N-:20]=[N+:21]=[N-:22].[Li+]>CN(C=O)C>[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[N:20]=[N+:21]=[N-:22])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 10779605HCID 10779605, compound

Product 1

HCID 10017261HCID 10017261, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4 (170 mg, 0.63 mmol) in DMF (5 ml) was treated with lithium azide (270 mg, 5.52 mmol) and stirred for two days at room temperature. The solvent was evaporated under reduced pressure at 40° C. and the crude oil was recrystallized from MeOH to obtain pure 5 (67 mg, 38.4%): mp 185-190° C. (dec.); UVλmax (water) pH 2: 205.0 (15,506), 287.0 (6,496); pH 7: 208.5 nm (12,943), 287.5 nm (6033); pH 11: 222.5 nm (6,730); 1H NMR (DMSO-d6) δ 3.66-3.90 (m, 3H, H-5′, H-4′), 4.16-4.33 (m, 2H, H-2′, H-3′), 5.14 (t, 1H, 5′-OH, exchangeable with D2O), 6.50 (d, 1H, H-1′), 8.75 (s, 1H, H-8), 10.12 (s, 1H, H-2); IR (KBr) 2037, 1649; Anal. (C10H11N7O4&Circlesolid;0.65 CH3OH): C, H, N.

Workup

  1. customThe solvent was evaporated under reduced pressure at 40° C.
  2. customthe crude oil was recrystallized from MeOH

Sources & evidence

ORD record
ord-41aa7449656f4bc6a1f40e41354beaa7
Source dataset
uspto-grants-2001_08
Patent number
US06271212B1

Reaction notes

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