Sodium Hydroxide → HCID 59134355, compound

HRID 1993493Notes

Reaction equation

HRID 1993493 reaction equation
Cl[CH2:2][S:3]([NH:6][C:7]1[C:28]([OH:29])=[CH:27][C:10]2[C@H:11]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:12]([OH:17])[C:13]([CH3:16])([CH3:15])[O:14][C:9]=2[CH:8]=1)(=[O:5])=[O:4].[OH-].[Na+].[Cl-].[NH4+]>CO>[CH3:15][C:13]1([CH3:16])[C@H:12]([OH:17])[C@@H:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[C:9](=[CH:8][C:7]3[NH:6][S:3](=[O:5])(=[O:4])[CH2:2][O:29][C:28]=3[CH:27]=2)[O:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 59134397HCID 59134397, compound

Product 1

HCID 59134355HCID 59134355, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-Chloro-N-{(3R*,4S*)-3,6-dihydroxy-2,2-dimethyl-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-1-benzopyran-7-yl} methanesulfonamide (220 mg, 0.50 mmol) in methanol (2.2 mL), 1 mol/L sodium hydroxide aqeuous solution (1.00 mL, 1.00 mmol) was added, and the resulting mixture was stirred at room temperature for 3 hours. Then, the temperature was raised to 50° C., and the mixture was further stirred for 2 hours. Upon the completion of the reaction, the solution was cooled on standing, neutralized with saturated aqueous ammonium chloride solution, extracted 4 times with chloroform, and dried over anhydrous sodium sulfate. The solvent was distilled off and the aimed product was obtained (yield: 37%).

Workup

  1. temperatureThen, the temperature was raised to 50° C.
  2. stirringthe mixture was further stirred for 2 hours
  3. customUpon the completion of the reaction
  4. temperaturethe solution was cooled
  5. extractionextracted 4 times with chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-05b9fa2c65c94731a0633075d9486fd9
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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