Ammonia → HCID 21137747, compound

HRID 1358571Notes

Reaction equation

HRID 1358571 reaction equation
C([S:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:22]([CH3:23])[C:21]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:20]=3[N:19]=2)=[CH:12][CH:11]=1)[C:6]([OH:8])=O)(=O)C.C([N:32](CC)CC)C.ClCCOC=O.N>CN(C)C=O.O1CCCC1>[SH:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:22]([CH3:23])[C:21]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:20]=3[N:19]=2)=[CH:12][CH:11]=1)[C:6]([NH2:32])=[O:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 2467482-Chloroethyl formateHCID 86587627HCID 86587627, compound

Product 1

HCID 21137747HCID 21137747, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-acetylthio-3-[4-(6-methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenyl]propionic acid (1.53 g), anhydrous triethylamine (0.4 g), chloroethylformate (0.65 g), anhydrous tetrahydrofuran (10 ml) and anhydrous N,N-dimethylformamide (10 ml) was stirred at room temperature for 1 hour. An aqueous solution of ammonia (20 ml, 28%) was added to the reaction mixture and this mixture was stirred for 2 hours and then allowed to stand overnight. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by liquid chromatography (LiChroprepNH2 (Merck)) using ethanol:ethyl acetate=1:12 as the eluant to afford the title compound (0.21 g, mp 204-208° C.) as a pale yellow powder.

Workup

  1. stirringthis mixture was stirred for 2 hours
  2. waitto stand overnight
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by liquid chromatography (LiChroprepNH2 (Merck))

Sources & evidence

ORD record
ord-f5ba773bfe0143678a789d41d46c62e7
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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