Hydrochloric Acid → HCID 11059916, compound

HRID 1420300Notes

Reaction equation

HRID 1420300 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[C:57]2[N:56]=[C:55]([Cl:58])[N:54]=[C:38]([NH:39][CH2:40][CH:41]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:37]=2[N:36]=[CH:35]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[NH3:34].[Cl:58][C:55]1[N:54]=[C:38]([NH:39][CH2:40][CH:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:37]2[N:36]=[CH:35][N:34]([C:57]=2[N:56]=1)[C@@H:11]1[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21308731HCID 21308731, compound

Product 2

HCID 222AmmoniaHCID 11059916HCID 11059916, compoundYield 186.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

2-Chloro-N-(2,2-diphenylethyl)-adenosine 2',3',5'-tribenzoate (71.2 g) in methanol (980 ml) was treated with potassium carbonate (52.1 g). The suspension was stirred at 22° C. for 2 h. It was then acidified to pH 8 with concentrated hydrochloric acid, evaporated and purified on flash silica (2 kg) eluting with dichloromethane:ethanol:0.880 ammonia (90:10:1) to give the title compound (40.2 g) as a white solid, nmr(δ,DMSO-d6) 3.58(m,1H), 3.65(m,1H), 3.84(br.s,1H), 4.0 to 4.2 and 4.4 to 4.65(2 m,5H), 5.04(t,1H), 5.22 (d,1H), 5.48 (d,1H), 5.82(m,1H), 7.1 to 7.4(m,10H), 8.33(s,1H), 8.42(t,1H).

Workup

  1. customevaporated
  2. custompurified on flash silica (2 kg)
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-08555ceda6a44e1397dabc4a8563c642
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

Loading…