Ammonium Chloride → HCID 86617193, compound

HRID 1993488Notes

Reaction equation

HRID 1993488 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7]([OH:28])=[CH:8][C:9]2[O:14][C:13]([CH3:16])([CH3:15])[C@@H:12]([OH:17])[C@H:11]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[CH:27]=1)=[O:4].[Cl-].[NH4+]>CO.[OH-].[Na+]>[OH:17][C@H:12]1[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[CH:27]=[C:6]3[C:7]([O:28][CH2:2][C:3](=[O:4])[NH:5]3)=[CH:8][C:9]=2[O:14][C:13]1([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86617194HCID 86617194, compound

Product 1

HCID 86617193HCID 86617193, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-chloro-N-{(±)-trans-3,7-dihydroxy-2,2-dimethyl-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-1-benzopyran-6-yl}-acetamide (187 mg, 0.46 mmol) in methanol (2 mL), sodium hydroxide aqueous solution (1 mol/L, 1.8 mL) was added at room temperature, and the resulting mixture was stirred for 3 hours. Upon the completion of the reaction, saturated ammonium chloride aqeuous solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with 1 mol/L sodium hydroxide aqueous solution and then with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/3) and the aimed product was obtained (yield: 61%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with 1 mol/L sodium hydroxide aqueous solution
  4. dry with materialwith saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-0318ac35444449948d2b5965301b905f
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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