Hydrochloric Acid → HCID 11059916, compound

HRID 582527Notes

Reaction equation

HRID 582527 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-(2,2diphenylethyl)-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 2h. 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,1 H), 4.0 to 4.2 and 4.4 to 4.65 (2m,5H), 5.04 (t,1 H), 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-bcf72e9bdf604fda9133a2e646c6e53e
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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