Ammonia → HCID 13934548, compound

HRID 1418825Notes

Reaction equation

HRID 1418825 reaction equation
C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.[C@H:13]1([N:22]2[CH:29]=[CH:28][C:26]([NH2:27])=[N:25][C:23]2=[O:24])[O:21][CH2:20][C@H:18]([OH:19])[C@H:16]([OH:17])[C@@H:14]1[OH:15].N>>[C@H:13]1([N:22]2[CH:29]=[CH:28][C:26]([NH2:27])=[N:25][C:23]2=[O:24])[O:21][CH2:20][C@H:18]([OH:19])[C@H:16]([OH:17])[C@@H:14]1[OH:15]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 69821750HCID 69821750, compound

Product 1

HCID 13934548HCID 13934548, compoundYield 17%

Procedure

β-L-ribopyranosylcytosine triacetate (7) was deprotected by treating with 2.0M methanolic ammonia (80 ml for 10 mmol nucleoside) for 24 h at room temperature. The methanolic ammonia was evaporated in vacuo and the residue was purified by flash chromatography on silica gel (150 g) with chloroform-methanol-water (65:35:4) eluent to give (8) 0.8 g (17% overall yield) of white needles. TLC:Rf =0.17 in chloroform-methanol-water (65:35:4) as a mobile phase.

Workup

  1. customThe methanolic ammonia was evaporated in vacuo
  2. customthe residue was purified by flash chromatography on silica gel (150 g) with chloroform-methanol-water (65:35:4) eluent

Sources & evidence

ORD record
ord-054516aa9774441a80f45ea83a847917
Source dataset
uspto-grants-1999_03
Patent number
US05885972

Reaction notes

Loading…