HCID 12043201, compound → HCID 20598923, compound

HRID 478769Notes

Reaction equation

HRID 478769 reaction equation
[NH2:1][C:2]1[N:6]([C@H:7]2[O:19][C@@H:18]([CH2:20][O:21]C(=O)C)[C@H:13]([O:14]C(=O)C)[C@@H:8]2[O:9]C(=O)C)[N:5]=[N:4][C:3]=1[C:25]([NH2:27])=[O:26]>N>[NH2:1][C:2]1[N:6]([C@H:7]2[O:19][C@@H:18]([CH2:20][OH:21])[C@H:13]([OH:14])[C@@H:8]2[OH:9])[N:5]=[N:4][C:3]=1[C:25]([NH2:27])=[O:26]

Participants

3

Reactant 1

HCID 12043201HCID 12043201, compound

Product 1

HCID 20598923HCID 20598923, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Compound 36 (0.5 g, 1.29 mmol) was dissolved in methanolic ammonia (50 mL, sat. at 0° C.). The reaction mixture was stirred at room temperature for 16 h and evaporated to dryness. The residue was triturated thrice with EtOAc and the solid was crystallized from minimum amount of dry EtOH to yield colorless solid: mp 159-161° C.; 1H NMR (Me2SO-d6) δ3.40-3.52 (m, 2H, C5′H), 3.93 (m, 1H, C4′H), 4.19 (m, 1H, C3′H), 4.46 (m, 1H, C2′H) 4.74, 5.22, 5.62 (m, 3H, 3 OH, D2O exchangeable), 5.84 (d, 1H, J=3.90 Hz, C1′H), 7.95 (br s, 2H) and 9.02 (br s, 2H). Anal. Calc. for C8H13N5O5 (259.22): C, 37.07; H, 5.05; N, 27.02. Found: C, 37.36; H, 5.14; N, 27.01.

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated thrice with EtOAc
  3. customthe solid was crystallized from minimum amount of dry EtOH
  4. customto yield colorless solid

Sources & evidence

ORD record
ord-8e2bf9014d0a4413b2d51587f082793d
Source dataset
uspto-grants-2003_11
Patent number
US06642206B2

Reaction notes

Loading…