Sodium Hydroxide → HCID 67455120, compound

HRID 1713330Notes

Reaction equation

HRID 1713330 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:14]=[CH:15][C:16]=1[CH2:17][NH:18][C:19]1[N:20]([C:30]2[N:31]=[CH:32][N:33]=[C:34]([NH2:37])[C:35]=2[N:36]=1)[C@@H:21]1[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[C@H:22]1[OH:23])=[O:5])C.[OH-].[Na+]>CO>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:14]=[CH:15][C:16]=1[CH2:17][NH:18][C:19]1[N:20]([C:30]2[N:31]=[CH:32][N:33]=[C:34]([NH2:37])[C:35]=2[N:36]=1)[C@@H:21]1[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[C@H:22]1[OH:23])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67456514HCID 67456514, compound

Product 1

HCID 67455120HCID 67455120, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-[3-(4-ethoxycarbonylbutoxy)-biphenyl-4-ylmethylamino]adenosine (0.077 g) in methanol (1.3 mL) was added 2 mol/L aqueous sodium hydroxide (0.098 mL), and the resulting mixture was stirred at room temperature for 21 hours and then at 50° C. for 2 hours. Two mol/L aqueous sodium hydroxide (0.098 mL) was added and stirring was continued for additional 64 hours. The reaction mixture was cooled to room temperature, quenched by addition of 2 mol/L hydrochloric acid (0.227 mL) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=4/1) to give the title compound (0.083 g).

Workup

  1. waitat 50° C. for 2 hours
  2. stirringstirring
  3. waitwas continued for additional 64 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customquenched by addition of 2 mol/L hydrochloric acid (0.227 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=4/1)

Sources & evidence

ORD record
ord-69f6e9dcd6ea4ccc9dbd8a8ac8138d65
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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