Ammonia → HCID 59107257, compound

HRID 966394Notes

Reaction equation

HRID 966394 reaction equation
[H][H].[NH3:3].C([O:8][C:9](=[O:40])[CH2:10][O:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[CH:17][N:18]2[C@@H:21]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@@H:27]([O:28]C(=O)C)[C@H:22]2[O:23]C(=O)C)=[C:14](Cl)[N:13]=1)(C)(C)C>>[C:9]([CH2:10][O:11][C:12]1[N:13]=[C:14]([NH2:3])[C:15]2[N:16]=[CH:17][N:18]([C:19]=2[N:20]=1)[C@@H:21]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:27]([OH:28])[C@H:22]1[OH:23])([OH:8])=[O:40]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 59107265HCID 59107265, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59107257HCID 59107257, compoundYield 70%

Procedure

A compound having a structure of the above formula was prepared where the substituents R1 and R2 are hydrogen and R3 is —CH2COOH. The compound (C12H15N5O7) was prepared by reaction of ammonia with (6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuran-osyl)purin-2-yl)oxyacetic acid tert-butyl ester (Example 6) as described in Example 2, Step E. The final product was isolated in 70% yield as a solid with a melting point of 200-203° C. 1H-NMR (DMSO-d6): δ 3.4 (m, 1H); 3.55 (m, 1H); 3.91 (m, 1H); 4.11 (m, 1H); 4.56 (m, 1H); 4.74 (bs, 1H); 4.78 (s, 2H); 5.3 (bs, 2H); 5.75 (d, 1H, J=6); 7.36 (bs, 2H); 8.15 (s, 1H); 12.6 (bs, 1H).

Workup

  1. customwas prepared where the substituents

Sources & evidence

ORD record
ord-79987a05ac16479b9c0fb06403810bdd
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

Loading…