Ammonium Chloride → HCID 59134293, compound

HRID 1993480Notes

Reaction equation

HRID 1993480 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:27]([OH:28])=[CH:26][C:9]2[C@H:10]([NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:11]([OH:16])[C:12]([CH3:15])([CH3:14])[O:13][C:8]=2[CH:7]=1)=[O:4].[Cl-].[NH4+]>CO.[OH-].[Na+]>[OH:16][C@@H:11]1[C@@H:10]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]2[CH:26]=[C:27]3[C:6]([NH:5][C:3](=[O:4])[CH2:2][O:28]3)=[CH:7][C:8]=2[O:13][C:12]1([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 59134290HCID 59134290, compound

Product 1

HCID 59134293HCID 59134293, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-chloro-N-[(3R*,4S*)-3,6-dihydroxy-2,2-dimethyl-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-1-benzopyran-7-yl]-acetamide (120 mg, 0.30 mmol) in methanol (1.2 mL), aqueous sodium hydroxide solution (1 mol/L, 1.5 mL) was added at room temperature, and the resulting mixture was stirred for 4 hours. Upon the completion of the reaction, saturated aqueous ammonium chloride solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated aqueous sodium hydroxide solution (1 mol/L) 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=1/1) and the aimed product was obtained (yield: 72%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydroxide solution (1 mol/L)
  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=1/1)

Sources & evidence

ORD record
ord-8ef4f901273448c293ae99356c83b537
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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